Reacción #93540

Ecuación de reacción

triethylamine

o-fluorobenzoic acid

α-mercaptomethyl-β-phenyl-γ-butyrolactone

diphenylphosphoryl azide

→

title compound

Rendimiento 67.2%

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

Rendimiento 67.2%

Disolventes

dimethylformamide

ethyl ether

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with 5% hydrochloric acid, saturated aqueous sodium hydrogencarbonate, and saturated saline
2. 2
   Secadodried over magnesium sulfate
3. 3
   workup.DISTILLATIONthe solvent was then distilled off
4. 4
   OtroThe crude product thus obtained
5. 5
   Otrowas purified by a silica gel column chromatography

Procedimiento

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.

Fuente