반응 #1369806

반응 방정식

water

sodium thiomethoxide

1-(4-bromobutyl)cyclopentane carboxylic acid methyl ester

sodium thiomethoxide

→

colorless oil

수율 51.0%

1-[4-(Methylthio)butyl]cyclopentane Carboxylic Acid Methyl Ester

수율 51.0%

용매

DMF

반응 조건

후처리

1. 1
   추출The organic compound was extracted with ether (2×150 mL)
2. 2
   세척The combined extracts were washed with brine (150 mL)
3. 3
   건조dried over anhydrous magnesium sulfate
4. 4
   여과After filtration of the drying agent
5. 5
   농축the solution was concentrated under vacuum
6. 6
   기타the resulting residue was purified by silica gel column chromatography

실험 절차

To a solution of 1-(4-bromobutyl)cyclopentane carboxylic acid methyl ester (38 mmol, 10 g) in DMF (100 mL) was added sodium thiomethoxide (72.6 mmol, 5.09 g). After addition of sodium thiomethoxide, the reaction was exothermic and the mixture became a light brown cloudy solution. The mixture was stirred for 15 h at room temperature and was poured into water (200 mL). The organic compound was extracted with ether (2×150 mL). The combined extracts were washed with brine (150 mL) and dried over anhydrous magnesium sulfate. After filtration of the drying agent, the solution was concentrated under vacuum and the resulting residue was purified by silica gel column chromatography to afford 4.43 g (51%) of a colorless oil. LR MS (C12H22O2S): 230 (M+).

출처