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[ CAS No. 78191-00-1 ] {[proInfo.proName]}

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Chemical Structure| 78191-00-1
Chemical Structure| 78191-00-1
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Product Details of [ 78191-00-1 ]

CAS No. :78191-00-1 MDL No. :MFCD00060098
Formula : C4H9NO2 Boiling Point : -
Linear Structure Formula :H3CC(O)N(CH3)OCH3 InChI Key :OYVXVLSZQHSNDK-UHFFFAOYSA-N
M.W : 103.12 Pubchem ID :537505
Synonyms :

Safety of [ 78191-00-1 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501 UN#:1993
Hazard Statements:H225 Packing Group:Ⅲ
GHS Pictogram:

Application In Synthesis of [ 78191-00-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 78191-00-1 ]

[ 78191-00-1 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 67442-07-3 ]
  • [ 78191-00-1 ]
  • 2
  • [ 1583-59-1 ]
  • [ 125941-14-2 ]
  • [ 865-47-4 ]
  • [ 78191-00-1 ]
  • [ 126120-83-0 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane; EXAMPLE 3 Preparation of 4-acetyl-<strong>[1583-59-1]2,2-difluoro-1,3-benzodioxole</strong> 6.2 g (55 mmol) of potassium tert.-butoxide dissolved in 40 ml of tetrahydrofuran (THF) are added dropwise at -30 C. under argon, over a period of 20 minutes, to a solution of 8.0 g (50 mmol) of <strong>[1583-59-1]2,2-difluoro-1,3-benzodioxole</strong> in 10 ml of THF in a 250 ml 3-necked flask. The mixture is then cooled to -90 C. (methanol/liquid nitrogen), and 35 ml (55 mmol) of n-butyllithium (1.58M in hexane) are added thereto over a period of 30 minutes. The deep red solution of 2,2-difluoro-1,3-benzodioxol-4-yl-potassium is maintained at -78 C. for 20 minutes. Then, 5.2 g (50 mmol) of N-methyl-N-methoxy-acetamide in 20 ml of THF are added thereto over a period of 15 minutes at -78 C. When the dropwise addition is complete, the beige reaction mixture is allowed to warm up to -10 C. and is then hydrolyzed with 40 ml of 10% hydrochloric acid. The hydrolyzed mixture is extracted three times with 70 ml of diethyl ether each time. The organic solutions are washed three times with 30 ml of 1N HCl each time, dried over Na2SO4 and concentrated in a vacuum rotary evaporator. Upon distillation of the residue, 7.1 g (79%) of the product distil over in the form of a colourless oil at boiling point (b.p.) 114-116 C./30 mbar. 1 H NMR (CDCl3; 300 MHz): 7.65 (d x d; J 7.9; 1.5; 1H); 7.27 (d x d; J 7.9; 1.5; 1H); 7.18 (t; J 7.9; 1H); 2.68 (s; 3H).
  • 3
  • [ 15803-02-8 ]
  • [ 78191-00-1 ]
  • [ 37687-18-6 ]
YieldReaction ConditionsOperation in experiment
57% A. Synthesis of 1-(1-methyl-1H-pyrazol-4-yl)ethanone 4-Bromo-1-methyl-1H-pyrazole (41.3 mL, 400 mmol), was dissolved in tetrahydrofuran (750 mL) and cooled to -78 C. N-Butyllithium (2.5 M solution in hexanes, 160 mL, 400 mmol) was added drop-wise over 30 minutes, and the resulting mixture was stirred for 1 hour at -78 C. After drop-wise addition of a solution of N-methoxy-N-methylacetamide (40.9 mL, 400 mmol) in tetrahydrofuran (100 mL) to the -78 C. reaction mixture, the cooling bath was allowed to warm to 0 C. over 4 hours. The reaction was then quenched with saturated aqueous sodium chloride solution (50 mL), and volatiles were removed in vacuo. The residue was diluted with ethyl acetate (1000 mL), treated with magnesium sulfate, and stirred for 30 minutes before being filtered and concentrated in vacuo. Purification was carried out via silica gel chromatography (material was loaded in a minimum amount of dichloromethane; Gradient: 5% to 100% ethyl acetate in heptane) to provide a pale yellow oil that solidified on standing. Yield: 28.5 g, 230 mmol, 57%. 1H NMR (500 MHz, CDCl3) delta 2.37 (s, 3H), 3.90 (s, 3H), 7.83 (s, 1H), 7.84 (s, 1H).
  • 4
  • [ 5433-01-2 ]
  • [ 78191-00-1 ]
  • [ 40428-87-3 ]
YieldReaction ConditionsOperation in experiment
66% Into a 500-mL round-bottom flask purged and maintained with an inert atmosphere of N2 was placed a solution of 1-bromo-3- (propan-2-yl)benzene (5.0 g, 25.11 mmol, 1.00 equiv) in THF (250 mL). This was followed by the addition of n-BuLi (20 mL, 2.00 equiv) dropwise with stirring at -60 C. The mixture was stirred at -60C for 30 mm. To this was added N-methoxy-N-methylacetamide (3.9 g, 37.82 mmol, 1.50 equiv) dropwise with stirring at -30 C. The resulting solution was stirred for 3 h at -30 C in a liquid N2 bath. The reaction was then quenched by the addition of 20 mL of water. The resulting solution was diluted with 200 mL of EtOAc, washed with 2x100 mL of brine, dried over anhydrous Na2SO4 and concentrated under vacuum. The residue was applied onto a silica gel column with EtOAc/petroleum ether (1:10). This resulted in 2.7 g (66%) of the title product as colorless oil.
To a solution of 1 -bromo-3-isopropylbenzene (10 g, 0.05 moi) in THF was added dropwise with BuLi (47 ml,, 0.075 niol) at -60 'C. After stirred 30 minutes, N-methoxy-N-methyiacetamide (6.22 g, 0.06 mol) was added. The mixture was stirred at -30C for 3 hours. Then the mixture was quenched with H20, the mixture was partitioned between EtOAc and water. The layer was separated and washed with water, brine, dried over Na2SC>4, and concentrated. The residue was purified by column chromatography to obtained the titled compound. ? NMR (CHLQRQFORM-d): delta 7.85 (s, i l l ). 7.79 (dt, j = 7.6, 1 .4 Hz, 1H), 7.33 - 7.53 (m, 2H), 3.00 (dt, J - 13.8, 6.9 Hz, 1H), 1.30 (d, J - 6.7 Hz, 6H)
To a solution of l-bromo-3-isopropylbenzene (10 g, 0.05 niol) in THF was added dropwise with BuLi (47 mL, 0.075 mol) at -60C. After stirred 30 minutes, -methoxy- -methylacetamide (6,22 g, 0.06 mol) was added. The mixture was stirred at -30C for 3 hours. Then the mixture was quenched with H20, the mixture was partitioned between EtOAc and water. The layer was separated and washed with water, brine, dried over Na2S04, and concentrated. The residue was purified by column chromatography to obtained the titled compound. 'H NMR (CHLOR OFQRM-d) : delta 7.85 (s, 1H), 7.79 (dt, J = 7.6, 1.4 Hz, 1H), 7.33 - 7.53 (m, 2H), 3.00 (dt, J - 13.8, 6.9 Hz, 1H), 1.30 (d, J - 6.7 Hz, 6H) LC-MS : m/z 163(M+H)+
To a solution of Compound 59A (3.96 g, 20 mmol) in dry THF (20 mL) at - 78 C was dropped a solution of n-BuLi in THF (2.5 M, 8 mL, 18 mmol). After stirred at - 78 C for 1 hour, to the mixture was dropped N-methoxy-N-methylacetamide (1.87 g, 18 mmol). The mixture was stirred at -78 C for 0.5 hour, quenched with water (10 mL), and extracted with ethyl acetate (20 mL x 3). The combined organic layers was washed with brine (40 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, from 0% to 8% v/v) to yield Compound 59B: LC-MS (ESI) m/z: 163 [M+H]+;1H-NMR (CDCl3, 400 MHz): delta (ppm) 1.27 (d, J =7.2.4 Hz, 6H), 2.60 (s, 3H), 2.93-3.00 (m, 1H), 7.38 (t, J = 7.6 Hz, 1H), 7.44 (t, J = 7.2Hz, 1H), 7.76 (d, J = 7.2 Hz, 1H), 7.83 (s, 1H).

  • 5
  • [ 3430-16-8 ]
  • [ 78191-00-1 ]
  • [ 42972-46-3 ]
YieldReaction ConditionsOperation in experiment
To 3-bromo-5-methylpyridine 1-1 (2 g, 11.63 mmol) in diethyl ether (30 ml) at -78 C was added uLi (8.72 ml, 13.95 mmol) dropwise. After 30 min, N-methoxy-N- methylacetamide n-BuLi was added. The resulting mixture was stirred at -78 C for 2 h then at rt overnight, quenched with saturated NH4CI solution and diluted with EtOAc. The organic layer was washed with water, brine, dried over magnesium sulfate and concentrated to give a yellow residue, which was purified by column chromatography (0-65% EtOAc in hexane) to give the desired product 1-2: 1H NMR (400 MHz, CDCI3) δ 8.98 (s, IH), 8.62 (s, IH), 8.04 (s, IH), 2.63 (s, 3H)5 2.41 (s, 3H).
  • 6
  • [ 79762-54-2 ]
  • [ 78191-00-1 ]
  • [ 189559-85-1 ]
YieldReaction ConditionsOperation in experiment
9% A. l-(lH-indazol-6-yl)ethanone (24-a) [00303] To a solution of 6-bromo-lH-indazole (5.0 g, 25.4 mmol) in 40 mL THF was added dropwise n-BuLi (2.5M, 30mL, 76.2 mmol) at -65 C, and the mixture was stirred for 2 h. Then, N-methoxy-N-methylacetamide (2.9 g, 27.9 mmol) was added. The reaction mixture was stirred for another 2 h at -65 C, then quenched with 40 mL H20. The mixture was extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with 100 mL brine, dried, and concentrated to dryness. The residue was purified by flash column chromatography (PE/EA=40/1) to give the title compound 24-a (370 mg, 9%) as a yellow solid. [M+H] Calc'd for C9H8N20, 161; Found, 161.
  • 7
  • [ 78191-00-1 ]
  • [ 20075-26-7 ]
  • [ 1007596-37-3 ]
  • 8
  • [ 39806-90-1 ]
  • [ 78191-00-1 ]
  • [ 37687-18-6 ]
YieldReaction ConditionsOperation in experiment
1-(1-Methyl-1H-pyrazol-4-yl)ethan-1-ol. To a resealable vial was added 4-iodo-1-methyl-1H-pyrazole (772 mg, 3.71 mmol), THF (6 mL), and the solution was cooled to 0 C. To this solution was added isopropylmagnesium chloride lithium chloride complex solution (3.42 mL, 4.45 mmol) and the reaction stirred for 30 min (complete disappearance of iodo-pyrazole as detected via LCMS) before cooling to -78 C and addition of N-methoxy-N-methylacetamide (1.18 mL, 11.13 mmol). The solution was stirred at -78 C for 1 h before removing the cold bath and warming to ambient temperature. The solution was diluted with EtOAc and quenched via the addition of 1N HCl. The layers were separated and the aqueous was extracted with EtOAc. The combined organics layer was washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was taken up in MeOH and cooled to 0 C before addition of NaBH4 (281 mg, 7.42 mmol). The reaction was stirred while warming to ambient temperature and quenched when LCMS showed disappearance of starting material. This solution was then diluted with 1N HCl and EtOAc. The layers were separated and the aqueous was extracted with EtOAc (3X). The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. The crude material was purified via silica gel chromatography (MeOH:DCM) to afford 1-(1-methyl-1H-pyrazol-4-yl)ethanol
  • 9
  • [ 3141-24-0 ]
  • [ 78191-00-1 ]
  • [ 80775-52-6 ]
YieldReaction ConditionsOperation in experiment
28% Compound 25-3 (0444) 25-2 (9.5 g, 30 mmol) was dissolved in anhydrous THF (100 mL) and cooled to -78 C. To the above solution was added dropwise n-BuLi (8 mL, 21 mmol) for 30 min and stirred for 30 min. 25-1 was added dropwise at -78 C., stirred for 30 min and allowed to warm to rt before quenching with saturated ammonium chloride. The organic phase was separated and washed with brine, dried with anhydrous Na2SO4, filtered and concentrated to afford yellow oil, which was purified by column chromatography (elution: PE/EA=10/1) afford 25-3 as a yellow solid (2.3 g, 28%).
  • 10
  • [ 78191-00-1 ]
  • [ 18087-73-5 ]
  • [ 453548-65-7 ]
YieldReaction ConditionsOperation in experiment
3.4 g Bromoimidazo [l, 2_b] pyridazine (6.8 g, 34.3 mmol) was dissolved in re-distilled anhydrous tetrahydrofuranLiter). A solution of ethyl magnesium bromide in tetrahydrofuran (1M, 51.5 ml) was slowly added dropwise at 0 C under nitrogen.And stirred for 30 minutes, a solution of N-methoxy-N-methylacetamide (7.1 g, 68.7 mmol) in tetrahydrofuran (30Ml) was slowly added dropwise to the system. The temperature of the reaction system was returned to room temperature and stirred for 10 hours. Water (50 ml) was added to the reactionAnd extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, concentrated and purified by column chromatography (petroleum ether: ethyl acetate = 10: 1To 1: 1) afforded the title compound 3 ? 4 g.
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