Hydrochloric Acid → HCID 21216804, compound

Participants

Reaction Conditions

Reaction Steps

A solution of α-[2-(4-fluorophenyl)ethyl]-3-pyridineacetonitrile (4 g) in tetrahydrofuran (30 ml) was added dropwise, under nitrogen atmosphere, to a stirred suspension of sodium amide (0.8 g) at 0° C. After complete addition (~20 minutes) the resultant mixture was stirred at 0° C. for 1 hour followed by 1 hour at room temperature. The mixture was then cooled to -40° C. and treated with dropwise addition of a solution of allyl bromide (2 g) in tetrahydrofuran (30 ml) to produce a reaction mixture. The reaction mixture was allowed to warm up to room temperature overnight, then neutralized with 10% hydrochloric acid and worked up by extraction with methylene chloride to produce a crude reaction product. The crude reaction product was then chromatographed on a silica gel column and eluted with 25% ethyl acetate in hexanes to give 3.7 g of 4-fluoro-α-(2-propenyl)-α-(3-pyridinyl)benzene-butanenitrile. The structure was confirmed by NMR spectroscopy.

Provenance & Evidence