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ChemicalBook CAS DataBase List BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE
88738-78-7

BIS(2,2,2-TRIFLUOROETHYL) (METHOXYCARBONYLMETHYL)PHOSPHONATE synthesis

3synthesis methods
The synthesis method of Bis(2,2,2-trifluoroethyl) (Methoxycarbonylmethyl) phosphonate is as follows: To a stirred solution of dried 18-crown-6 (4.53 g, 17.14 mmol), THF (20 mL), and Bis(2,2,2-trifluoroethyl) Phosphite (0.70 mL, 1.29 mmol), was added KHMDS (9.0 mL, 4.50 mmol, 0.5M in toluene) by syringe in a dropwise manner at -78 ℃. After 15 min, methyl chloroacetate (0.30 mL, 3.41 mmol) was added and the reaction mixture was allowed to stir for 4 hr at room temperature. The reaction mixture was diluted with EtOAc (20 mL) and then quenched with sat. ammonium chloride (50 mL). The aqueous layer was extracted with EtOAc (3 x 30 mL). The combined organic extracts were dried under anhydrous magnesium sulfate. Following filtration, the solvents were removed in vacuo. The crude product was then purified by flash column chromatography (33% EtOAc in hexanes, Rf = 0.22 in 33% EtOAc in hexanes) yielding Bis(2,2,2-trifluoroethyl) (Methoxycarbonylmethyl)phosphonate (766 mg, 2.41 mmol, 70.3%) as a yellow syrup.
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Yield:88738-78-7 94%

Reaction Conditions:

Stage #1:methyl 2-(bis((trimethylsilyl)oxy)phosphoryl)acetate with iodine;triphenylphosphine in chloroform at 20; for 0.25 h;Inert atmosphere;
Stage #2: with 1H-imidazole in chloroform at 20 - 50; for 0.75 h;Inert atmosphere;
Stage #3:2,2,2-trifluoroethanol in chloroform at 60; for 5 h;Inert atmosphere;

Steps:

Methyl Bis(2,2,2-trifluoroethyl)phosphonoacetate (Still-Gennari reagent, 1)
TMSBr (90 L, 0.691 mmol) was added at r.t. to a solution of trimethyl phosphonoacetate (2; 50.3mg, 0.276 mmol) in anhydrous CH2Cl2 (0.55 mL). After stirring at r.t. for 5 h under argon,evaporation of the reaction mixture in vacuo gave methyl2-{bis[(trimethylsilyl)oxy]phosphoryl}acetate (4), which was used without further purification.Ph3P (181 mg, 0.691 mmol) and I2 (175 mg, 0.691 mmol) were added to a solution of 4 in anhydrous CHCl3 (1.8 mL) at r.t. under argon. After stirring at r.t. for 15 min under argon, imidazole(188 mg, 2.76 mmol) was added. The reaction mixture was stirred for 15 min at r.t. and then for 30min at 50 °C. Afterwards, 2,2,2-trifluoroethanol (79 l, 1.10 mmol) was added and the reactionmixture was stirred at 60 °C for 5 h. After filtration of the reaction mixture, the filtrate wasevaporated in vacuo to give a crude product 1, which was purified by column chromatography[Silica Gel PSQ 60B: n-hexane-EtOAc (2:1)] to afford 1 (82.3 mg, 94%) as a colorless oil. IR (neat) 1747, 1265, 1174, 1072, 963 cm-1. 1H NMR (500 MHz, CDCl3) δ = 4.51-4.42 (m, 4H),3.78 (s, 3H), 3.17 (d, 2JH,P = 21.1 Hz, 2H). 13C NMR (125 MHz, CDCl3) δ = 165.2 (d, 2JC,P = 4.5Hz), 122.5 (qd, 1JC,F = 277.1 Hz, 3JC,P = 8.2 Hz), 62.7 (qd, 2JC,F = 38.2 Hz, 2JC,P = 5.5 Hz), 53.1,33.8 (d, 1JC,P = 145.1 Hz). HRMS (ESI): m/z [M + Na]+ calcd for C7H9F6O5PNa: 340.9990; found:340.9982. Anal. Calcd for C7H9F6O5P: C, 26.43; H, 2.85. Found: C, 26.28; H, 2.89.

References:

Sano, Shigeki;Matsumoto, Tomoya;Toguchi, Munehisa;Nakao, Michiyasu [Synlett,2018,vol. 29,# 11,art. no. ST-2018-U0114-L,p. 1461 - 1464] Location in patent:supporting information

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