Tetrabutylammonium Fluoride → HCID 22645417, compound

Participants

Reaction Steps

A solution of 1-hexyl-3,4-dimethyl-4-{3-[2-(trimethylsilyl)ethynyl]-phenyl}piperidine (Preparation 4, 150 mg, 0.40 mmol) in tetrahydrofuran (2 mL) was cooled to -70° C. and tetrabutylammonium fluoride (1.0 M in THF, 0.41 mL, 0.41 mmol) was added slowly. The reaction mixture was allowed to warm to room temperature gradually before being diluted with dichloromethane (10 mL) and water (10 mL). The phases were separated and the aqueous layer was further extracted with dichloromethane (2×10 mL). The combined organics were dried (Na2SO4) and the solvent evaporated in vacuo. The oily yellow residue was purified by column chromatography on silica gel (10 g) eluted with ethyl acetate:hexane 0.880 ammonia (10:89:1) to give the title compound as an oil (100 mg).

Provenance & Evidence