Sodium → HCID 20205053, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hyride (50% dispersion in mineral oil) (0.49 g, 10.2 mmol) in N,N-dimethylformamide (30 ml) cooled to 0° C. in an ice-bath was added dropwise with stirring a solution of methyl 2-benzylthio-5-trifluoromethylbenzoate (2.5 g, 7.7 mmol) in N,N-dimethylformamide (10 ml). The reaction mixture was stirred at 75° C. for 1.5 hours under a nitrogen atmosphere, cooled and then poured into ice containing 1N hydrochloric acid. Extraction was effected with diethyl ether. The combined organic extracts were washed three times with water, once with saturated aqueous sodium chloride solution, dried (sodium sulfate) and evaporated. The residue was subjected to chromatography on a column of silica gel (Merck No. 7734) that was eluted with 10:1 hexane-ether. Fractions containing pure product were combined and evaporated to give a white solid that was recrystallized from toluene; yield 490 mg (22%), m/z 1294 (M+.).

Provenance & Evidence