反応 #93540

反応方程式

triethylamine

o-fluorobenzoic acid

α-mercaptomethyl-β-phenyl-γ-butyrolactone

diphenylphosphoryl azide

→

title compound

収率 67.2%

α-(o-fluorobenzoylthiomethyl)-β-phenyl-γ-butyrolactone

収率 67.2%

溶媒

dimethylformamide

ethyl ether

反応条件

後処理

1. 1
   洗浄washed with 5% hydrochloric acid, saturated aqueous sodium hydrogencarbonate, and saturated saline
2. 2
   乾燥dried over magnesium sulfate
3. 3
   workup.DISTILLATIONthe solvent was then distilled off
4. 4
   その他The crude product thus obtained
5. 5
   その他was purified by a silica gel column chromatography

実験手順

To a solution of 1.2 g of o-fluorobenzoic acid and 1.5 g of α-mercaptomethyl-β-phenyl-γ-butyrolactone in 20 ml of dimethylformamide were added 1.9 ml of diphenylphosphoryl azide (DPPA) and then 1.2 ml of triethylamine under ice-cooling. Then, the mixture was raised to a room temperature and stirred for 18 hours. After completion of the reaciton, the reaction mixture was diluted with 200 ml of ethyl ether, washed with 5% hydrochloric acid, saturated aqueous sodium hydrogencarbonate, and saturated saline, dried over magnesium sulfate and the solvent was then distilled off. The crude product thus obtained was purified by a silica gel column chromatography to give 1.6 g (yield 67%) of the title compound.

出典