Methanol → HCID 54172140, compound

Participants

Reaction Steps

Acetyl chloride (171 μL, 2.4 mmol) is carefully added to 8 mL of dry methanol and the solution is stirred for 15 minutes. Methyl thioglycolate (257 μL, 2.9mmol) and dibenzosuberenol (Aldrich) (0.50 g, 2.4 mmol) are added, and the reaction is stirred for 5 minutes. The reaction is diluted with ethyl acetate and washed with saturated aqueous sodium bicarbonate, water, then brine. The organic phase is dried over magnesium sulfate, filtered, and concentrated in vacuo. The resulting oil is chromatographed on silica gel eluting with ethyl acetate:toluene:hexane (3:27:70) to give 0.62 g (87%) of methyl (5H-dibenzo[a,d]cyclohepten-5-yl-thio)acetate: melting point 74°-76° C.

Provenance & Evidence