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[ CAS No. 624-76-0 ] {[proInfo.proName]}

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Chemical Structure| 624-76-0
Chemical Structure| 624-76-0
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Product Details of [ 624-76-0 ]

CAS No. :624-76-0 MDL No. :MFCD00002830
Formula : C2H5IO Boiling Point : -
Linear Structure Formula :- InChI Key :QSECPQCFCWVBKM-UHFFFAOYSA-N
M.W : 171.97 Pubchem ID :12225
Synonyms :

Safety of [ 624-76-0 ]

Signal Word:Danger Class:6.1
Precautionary Statements:P501-P270-P262-P210-P264-P280-P370+P378-P361+P364-P301+P310+P330-P302+P352+P310-P403+P235-P405 UN#:2810
Hazard Statements:H300+H310-H227 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 624-76-0 ]

* 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 [ 624-76-0 ]

[ 624-76-0 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 624-76-0 ]
  • [ 42059-80-3 ]
  • [ 96626-13-0 ]
  • 2
  • [ 624-76-0 ]
  • [ 18162-48-6 ]
  • [ 101166-65-8 ]
YieldReaction ConditionsOperation in experiment
98% With 1H-imidazole; In dichloromethane; at 30℃; for 17h; (i) Preparation of (2-iodoethoxy)-tert-butyldimethylsilane To a stirred solution of 2-iodoethanol (17.2 g; 100 mmol) and imidazole (8.17 g; 120 mmol) in dichloromethane (100 mL) was added tert-butyldimethylsilyl chloride (15.83 g; 105 mmol) at such a rate that the reaction temperature did not rise above 30° C. Upon complete addition the solution was left stirring for 17 h, then washed with water (2*50 mL) and brine (50 mL) and dried over MgSO4. Evaporation of the solvent afforded the target compound (28.0 g; 97.8 mmol; 98percent) as a colourless liquid. 1H-NMR (400 MHz) (CDCl3): delta=3.83 (t, 2H, J=7.0 Hz), 3.83 (t, 2H, J=7.0 Hz), 3.20 (t, 2H, J=7 Hz), 0.90 (s, 9H), 0.08 (s, 6H) ppm.
90% With 1H-imidazole; In N,N-dimethyl-formamide; at 30 - 40℃; for 4h; Preparation of tert-butyl(2-iodoethoxy)dimethylsilane After 2-iodoethanol (1.72 g, 10 mmol) was dissolved in dimethylformamide (8 mL), imidazole (0.817 g, 12 mmol) and tert-butyldimethylsilyl chloride (1.66 g, 11 mmol) were added thereto, and the mixture was stirred for 4 hours at 30° C. to 40° C. Water (50 mL) was added to the reaction solution, and the result was extracted with an ethyl acetate/normal-hexane=1/1 solution (100 mL). The organic layer was washed again with salt water (30 mL*3), dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 2.85 g (90percent) of a target compound. This compound was used as it was for the next reaction without purification.
90% With 1H-imidazole; In N,N-dimethyl-formamide; at 30 - 40℃; for 4h; Preparation of tert-butyl(2-iodoethoxy)dimethylsilane After 2-iodoethanol (1.72 g, 10 mmol) was dissolved in dimethylformamide (8 mL), imidazole (0.817 g, 12 mmol) and tert-butyldimethylsilyl chloride (1.66 g, 11 mmol) were added thereto, and the mixture was stirred for 4 hours at 30°C to 40°C. Water (50 mL) was added to the reaction solution, and the result was extracted with an ethyl acetate/normal-hexane=1/1 solution (100 mL). The organic layer was washed again with salt water (30 mLx3), dried with anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 2.85 g (90percent) of a target compound. This compound was used as it was for the next reaction without purification.
With 2-(Dimethylamino)pyridine; N-ethyl-N,N-diisopropylamine; In dichloromethane; Step 2 tert-Butyl-(2-iodo-ethoxy)-dimethyl-silane To 2-iodoethanol (20 gm, 116 mmol) suspended in methylene chloride (500 mL) was added dimethylaminopyridine (100 mg) followed by diisopropylethylamine (30 mL, 174 mmol) and tert-butyldimethylsilyl chloride (19 gm, 128 mmol). The reaction was stirred overnight and the solvent was removed in vacuo and the residue was passed through a short column of silica gel and eluted with 95:5 methylene chloride: methanol. The desired fractions were combined and the solvent was removed in vacuo to give the desired product. 1 H NMR (400 MHz, CDCl3) delta 3.84 (dd, 2H); 3.20 (dd, 2H); 0.9 (m, 9H); 0.1 (m, 6H).
With 1H-imidazole; In dichloromethane; at 20℃; for 20h;Cooling with ice; Large scale; Step C (1,1 -dimethylethyl)(2-iodoethoxy)dimethylsilane .OTBDMS Iodoethanol (2.68 kg, 15.4 mol), CH2CI2 (12 L) and imidizaole (1.556 kg, 22.63 mol) were chilled in an ice bath. A solution of t-butyldimethylchlorosilane (2.536 kg, 16.32 mol) in CH2CI2 (2.5 L) was added to the reaction over a 2 h period. The resulting white suspension was allowed to warm to rt over an 18 h. The reaction was worked up by washing with water and brine). The organic layer was dried (MgSC^) and evaporated under reduced pressure to provide the product of Step C as a light yellow oil. FontWeight="Bold" FontSize="10" H NMR (400MHz, CDC13) delta = 3.75 (t, J = 7.0 Hz, 2 H), 3.11 (t, J = 7.0 Hz, 2 H), 0.77 - 0.89 (m, 10 H), 0.00 (s, 6 H).

  • 3
  • [ 624-76-0 ]
  • [ 51792-34-8 ]
  • [ 877459-72-8 ]
  • 4
  • [ 6086-21-1 ]
  • [ 624-76-0 ]
  • [ 1335280-64-2 ]
  • 5
  • [ 624-76-0 ]
  • [ 34334-96-8 ]
  • [ 1006950-51-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In acetonitrile; for 18h;Reflux; A solution of 5-methyl-3-nitro-lH-pyrazole (500 mg, 3.93 mmol) and potassium carbonate (1.08 g, 7.81 mmol) in acetonitrile (20 mL) was treated dropwise with 2- iodoethanol (2.00 g, 1 1.6 mmol) and the reaction stirred at reflux for 18 h. After this time, the reaction was cooled to room temperature, diluted with ethyl acetate (100 mL) and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and the resulting residue purified by chromatography (silica, gradient, heptane to 1 : 1 ethyl acetate/heptane) to afford 2-(5-methyl-3-nitro-lH-pyrazol-l-yl)ethanol as a white solid: NMR (400 MHz, DMSO-i?d 6.82 (s, 1H), 4.97 (t, J = 5.2 Hz, 1H), 4.19 (t, J = 5.2 Hz, 2H), 3.75 (q, J= 5.2 Hz, 2H), 2.35 (s, 3H).
With potassium carbonate; In acetonitrile; for 18h;Reflux; Example 7 Preparation of 2-(5-methyl-3-nitro-1H-pyrazol-1-yl)ethanol A solution of <strong>[34334-96-8]5-methyl-3-nitro-1H-pyrazole</strong> (500 mg, 3.93 mmol) and potassium carbonate (1.08 g, 7.81 mmol) in acetonitrile (20 mL) was treated dropwise with 2-iodoethanol (2.00 g, 11.6 mmol) and the reaction stirred at reflux for 18 h. After this time, the reaction was cooled to room temperature, diluted with ethyl acetate (100 mL) and filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure and the resulting residue purified by chromatography (silica, gradient, heptane to 1:1 ethyl acetate/heptane) to afford 2-(5-methyl-3-nitro-1H-pyrazol-1-yl)ethanol as a white solid: 1H NMR (400 MHz, DMSO-d6.) d 6.82 (s, 1H), 4.97 (t, J=5.2 Hz, 1H), 4.19 (t, J=5.2 Hz, 2H), 3.75 (q, J=5.2 Hz, 2H), 2.35 (s, 3H).
  • 6
  • [ 624-76-0 ]
  • [ 51814-19-8 ]
  • [ 1339961-03-3 ]
  • 7
  • [ 288-32-4 ]
  • [ 624-76-0 ]
  • [ 18162-48-6 ]
  • [ 101166-65-8 ]
YieldReaction ConditionsOperation in experiment
98% In dichloromethane; (i) Preparation of (2-iodoethoxy)-tert-butyldimethylsilane To a stirred solution of 2-iodoethanol (17.2 g; 100 mmol) and imidazole (8.17 g; 120 mmol) in dichloromethane (100 mL) was added tert-butyldimethylsilyl chloride (15.83 g; 105 mmol) at such a rate that the reaction temperature did not rise above 30° C. Upon complete addition the solution was left stirring for 17 h, then washed with water (2*50 mL) and brine (50 mL) and dried over MgSO4. Evaporation of the solvent afforded the target compound (28.0 g; 97.8 mmol; 98percent) as a colourless liquid. 1H-NMR (400 MHz) (CDCl3): delta=3.83 (t, 2H, J=7.0 Hz), 3.83 (t, 2H, J=7.0 Hz), 3.20 (t, 2H, J=7 Hz), 0.90 (s, 9H), 0.08 (s, 6H) ppm.
  • 8
  • [ 624-76-0 ]
  • [ 54396-44-0 ]
  • C10H12F3NO [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% at 90℃; for 6h;Inert atmosphere; a) Preparation of intermediate 52 A mixture of 2-iodoethanol (0.296 mL, 3.8 mmol) and 2-methyl-3-trifluoromethyl- aniline (1 g, 5.7 mmol) was heated at 90 °C under N2 atmosphere for 6 h.The resulting solid was dissolved in EtOAc and washed with 2M aq. NaOH solution. The organic layer was dried, filtered and concentrated to dryness. The crude product was purified by flash column chromatography (silica; EtOAc/hexane 0/100 to 50/50). The desired fractions were collected and concentrated in vacuo to yield intermediate 52 as an oil (0.711 g, 85percent).
  • 9
  • [ 624-76-0 ]
  • [ 67630-01-7 ]
  • [ 189744-27-2 ]
YieldReaction ConditionsOperation in experiment
1.8 kg With sodium carbonate; In acetonitrile; at 23 - 85℃; for 2h;Large scale; EXAMPLE 1 Preparation of 4-(bis-(2-hydroxyethyl)-amino-N-BOC-L-phenylalanine ethyl ester Into a suitable reactor A, 2.0 kg of N-BOC-L-phenylalanine ethyl ester and acetonitrile were loaded. The suspension was let under stirring until complete dissolution, maintaining the temperature at 23C and 1 .5 kg of sodium carbonate were then added. Subsequently, 3.2 L of 2-iodoethanol were added dropwise, the solution was heated up to 85C and these conditions were maintained for 2 hours. At the end of the reaction the mixture was quickly cooled down to 20C. In another suitable reactor B, 35L of water and 4 kg of Celite were loaded and the mixture was left under stirring for at least 5 minutes. The compound obtained into reactor A was transferred into reactor B and the suspension was kept under stirring for an hour. The suspension was filtered and washed with 12L of water. The wet Celite obtained into the reactor B and 140 L of ethyl acetate were loaded into a reactor C and the mixture was kept under stirring for 30 minutes then filtered by collecting the filtrate into a reactor D and letting the phases separate. The organic phase was distilled at reduced pressure. The residue was purified by chromatography using methylene chloride/ethyl acetate about 2:1 . About 1 .8 kg of 4-(bis-(2-hydroxyethyl)-amino-N-BOC-L-phenilalanine ethyl ester were then obtained.
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