Hydrochloric Acid → HCID 11762049, compound

Participants

Reaction Steps

A solution of (R)-3-[1-(3,4,5-trimethoxyphenyl)-methyl]butanolide [10.52 g, 0.04 mol; K. Lalami, D. Dhai, and E. Brown, Heterocycles, 27, 1131 (1988)] and 3,4,5-trimethoxybenzaldehyde (11.4 g, 0.058 mol) in toluene (150 ml) was cooled to 0° C. under an argon stream. The solution was added with 4.0 g of sodium hydride (60%, 0.1 mol) and 0.15 ml (0.0037 mol) of methanol, followed by stirring at room temperature for 45 hours. The reaction mixture was ice-cooled and then added with 100 ml of 2N-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 solvent was distilled off. The residue thus obtained (20 g) was purified by column chromatography on a silica gel column (silica gel: "MERCK #9385", 500 g, eluent: 1:2 mixed solvent of ethyl acetate and hexane), whereby 5.71 g of the title compound were obtained as pale yellow oil (yield: 33%). [α]27D : -75.64° (C=0.55, CHCl3)

Provenance & Evidence