Sodium hydride → HCID 67266739, compound

Participants

Reaction Steps

565 mg (7.65 mmol, 1.5 eq) of N-hydroxy-acetamidine in 50 ml of THF were treated at RT with 306 mg (7.65 mmol, 1.5 eq) of NaH portionwise within 30 min. 1.0 g (5.1 mmol) of phenylsulfanyl-acetic acid ethyl ester was added in a THF solution, and stirring was continued for 1 hour at 60° C. The reaction mixture was diluted with saturated aqueous NH4Cl, extracted with EtOAc, filtered and evaporated. Column chromatography on silica gel with EtOAc/heptane 1:1 yielded 480 mg (46%) of 3-methyl-5-phenylsulfanylmethyl-[1,2,4]oxadiazole as a colorless oil.

Provenance & Evidence