HCID 15078761, compound → HCID 15078748, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl Z-3-(2'-methylbenzylthio)-3-phenyl-2-propenoate (900 mg, 3.02 mmol) in THF (8 mL) was added dropwise through a double-ended needle to a solution of potassium tert-butoxide (1.02 g, 9.09 mmol) in THF (12 mL). An additional 2 mL of THF was used to rinse the ester into the reaction. The reaction was stirred 30 minutes at 25° C., then cooled in an ice bath and quenched by the addition of 7.0 mL of 2.0 N aqueous hydrochloric acid. The reaction was poured into 50 mL of saturated aqueous sodium chloride solution and extracted with 2×50 mL of ethyl acetate. The ethyl acetate layers were washed in succession with 50 mL of saturated aqueous sodium chloride, dried over sodium sulfate, filtered, and evaporated. Flash column chromatography on 45 g of silica gel, eluting with 500 mL of 4% ethyl acetate in hexane followed by 500 mL of 6% ethyl acetate in hexane, gave 3-hydroxy-2-(2'-methyl phenyl) 5-phenylthiophene as an oil weighing 421 mg. The product could be distilled bulb-to-bulb, bp (0.4 mm) 140°-150° C.

Provenance & Evidence