Hydrochloric Acid → HCID 18653276, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (R)-3-[1-(5-methoxy-3,4-methylenedioxyphenyl)methyl]butanolide (21.0 g, 0.084 mol) and 3,4,5-trimethoxybenzaldehyde (26.0 g, 0.133 mol) in toluene (350 ml) was cooled to 0° C. under an argon stream, followed by the addition of sodium hydride (60%, 9.1 g, 0.228 mol) and methanol (0.33 ml, 0.0082 mol). After stirred at 0° C. for 15 minutes and then at room temperature for 18 hours, the reaction mixture was ice cooled and then acidified with 2N-HCl. After the addition of ethyl acetate (100 ml), the organic layer was separated. The water layer was extracted with ethyl acetate (50 ml×2). The extracts were combined with the previously-obtained organic layer. The organic layer was washed successively with water, saturated NaHCO3 and saturated NaCl, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off. The residue thus obtained (52.9 g) was purified by column chromatography (silica gel: "MERCK #9385", 500 g, eluent: 1:2 mixed solvent of ethyl acetate and hexane), whereby 16.62 g of the title compound were obtained as colorless oil (yield: 46%). [α]27D : -53.7° (C=1.04, CHCl3)

Provenance & Evidence