Phenol → 1-(6.7-Dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-3-methyl-2-(phenoxy)butan-1-one

Participants

Reaction Conditions

Reaction Steps

Phenol (50 μl, 0.569 mmol) and sodium hydride (60% in a mineral oil, 10 mg) were added to a DMF (2 ml) solution of 1-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl)-3-methyl-2-bromobutan-1-one (54 mg, 0.152 mmol) obtained in Reference example 16, and the mixture was stirred at 80° C. for 10 hours and cooled to room temperature. The reaction solution was diluted with ethyl acetate and hexane (1:1, 50 ml), washed with a 1 N aqueous sodium hydroxide solution (30 ml) and 1 N hydrochloric acid (30 ml), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to preparative thin layer chromatography using ethyl acetate and hexane (1:1) as an eluent to obtain the captioned compound (30.7 mg, 55%) as a yellow oily substance.

Provenance & Evidence