Tetrabutylammonium Fluoride → HCID 22161798, compound

Participants

Reaction Steps

To a solution of 8-(t-butyldimethylsilyloxymethyl)-4-methoxy-3,3-dimethyl-1-ethyl-1,2,3,4-tetrahydroquinoline (1.40 g) in tetrahydrofuran (20 ml), 1M solution (4.2 ml) of tetrabutylammonium fluoride in tetrahydrofuran was added dropwise under ice-cooling. After the mixture was stirred for 45 minutes, tetrahydrofuran was distilled off and the residue was extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off. The resulting residue was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate (6:1)] to give 8-hydroxymethyl-4-methoxy-3,3-dimethyl-1-ethyl-1,2,3,4-tetrahydroquinoline (0.75 g).

Provenance & Evidence