methyl diphenylmethylmercaptoacetate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl thioglycolate (5.95 g, 56 mmol) in 225 mL of tetrahydrofuran is added sodium hydride (2.5 g of 60% NaH in oil, 62.5 mmol). The mixture is stirred at room temperature for 10 minutes. Benzhydryl bromide (Aldrich of Milwaukee, Wis.; hereinafter "Aldrich") (15.3 g, 62 mmol) is added and the reaction mixture is stirred at room temperature for 3 days and then concentrated in vacuo. The residue is taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate, 10% aqueous citric acid, and brine and then dried over magnesium sulfate. Chromatography on silica gel, eluting with 4% ethyl acetate in hexane provides methyl [[(diphenyl)methyl]thio]acetate as a colorless oil in 15% yield. hereinafter "Aldrich") (15.3 g, 62 mmol) is added the reaction mixture is stirred at room temperature for 3 days concentrated in vacuo washed with saturated aqueous sodium bicarbonate, 10% aqueous citric acid, and brine dried over magnesium sulfate Chromatography on silica gel, eluting with 4% ethyl acetate in hexane