반응 #71584

반응 방정식

sodium ethoxide

acetic acid

ethyl 3-acetylthio-2-methylbutyrate

→

objective compound

수율 56.6%

ethyl 3-mercapto-2-methylbutyrate

수율 56.6%

용매

ethanol

ethanol

반응 조건

후처리

1. 1
   기타ethanol was evaporated off under reduced pressure
2. 2
   workup.ADDITIONAfter addition of an aqueous sodium chloride solution
3. 3
   추출to the residue, extraction with diethyl ether
4. 4
   세척The organic layer was washed successively with a saturated aqueous sodium bicarbonate solution and brine (twice)
5. 5
   기타The solvent in the organic layer was evaporated off
6. 6
   workup.DISTILLATIONvacuum distillation (35 to 36° C./2 torr)

실험 절차

Under nitrogen atmosphere, a mixture of 40.00 g (0.192 mol) of ethyl 3-acetylthio-2-methylbutyrate and 800 ml of ethanol was cooled to −15° C., 72.01 g (0.212 mol, 1.1 Eq) of a 20% solution of sodium ethoxide in ethanol was added dropwise thereto over 1 hour, and the mixture was stirred for 3 hours. The reaction mixture was neutralized with 15.00 g of acetic acid, and then ethanol was evaporated off under reduced pressure. After addition of an aqueous sodium chloride solution to the residue, extraction with diethyl ether was performed. The organic layer was washed successively with a saturated aqueous sodium bicarbonate solution and brine (twice). The solvent in the organic layer was evaporated off, and vacuum distillation (35 to 36° C./2 torr) was performed to give 17.63 g of the objective compound (GC purity: 99.3%, yield: 56.1%, diastereomer ratio: 80.6/19.4).

출처