4-[3-(5-chloropentyloxy)phenyl]-4-hydroxy-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-2,3-dihydro-4H-benzopyran → 4-[3-(5-chloropentyloxy)phenyl]-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-2,3-dihydro-4H-benzopyran

Participants

Reaction Steps

4-[3-(5-Chloropentyloxy)phenyl]-4-hydroxy-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-2,3-dihydro-4H-benzopyran (307 mg, 0.56 mmol) was dissolved in methanol (15 ml), and 10% Pd/C (102 mg) was slowly added dropwise thereto. Then the reaction mixture was stirred under hydrogen atmosphere for 2 hours and filtered. The filtrate was concentrated under reduced pressure to remove the organic solvent. The concentrate was separated by column chromatography (n-hexane:ethyl acetate=8:1) to obtain 283 mg (yield: 95%, 3RS,4RS/3RS,4SR=1:1) of the title compound as a colorless oil.

Provenance & Evidence