Hydrochloric Acid → HCID 11144422, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-3-[1-(5-methoxy-3,4-methylenedioxyphenyl)methyl]butanolide (25.0 g, 0.1 mol) and 3,4,5-trimethoxybenzaldehyde (31.0 g, 0.16 mol) in 400 ml of toluene was cooled to 0° C. under an argon stream, followed by the addition of 10.8 g of sodium hydride (60%, 0.27 mol) and 0.4 ml (0.01 mol) of methanol. After stirred at 0° C. for 15 minutes and further at room temperature for 48 hours, the reaction mixture was ice-cooled and added with 100 ml of 6N-HCl. After the removal of the water layer, the organic layer was washed successively with water, saturated NaHCO3 and saturated NaCl, and then dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent was purified by column chromatography (silica gel: "MERCK #9385", 500 g, eluent: 1:2 mixed solvent of ethyl acetate and hexane), whereby 20.38 g of the title compound were obtained as colorless oil (yield: 48%).

Provenance & Evidence