Formic Acid → 4-[2-(5-Methyl-2-phenyloxazol-4-yl)ethoxy]benzaldehyde

Participants

Reaction Steps

A mixture of 6.0 g of 4-(2-phenyl-5-methyloxazol4-ylethoxy)benzonitrile (prepared by reacting p-fluorobenzonitrile with 2-phenyl-4-hydroxyethyl-5-methyloxazole), 6.0 g of Raney nickel alloy and 100 ml of 70% formic acid was heated to reflux for 2 hours. The reaction was cooled and the solids filtered and washed with ethyl acetate. The washings and formic acid filtrate were combined and concentrated in vacuo to an oil. The residue was treated with water (100 ml) and extracted with ethyl acetate (3×100 ml). The extracts were combined and washed with water until the pH of the washings was 7. The extracts were washed with a brine solution, dried over sodium sulfate and concentrated to an oil, which on chromatographing on 250 g of silica gel (ethyl acetate-hexane; 30:70; v:v) gave 5.08 g of product, m.p. 79°-81° C.

Provenance & Evidence