Pyridine → 2-Phenylbutyric Acid

Participants

Reaction Steps

A solution of 2,3-isopropylidene-D(+)-ribono-1,4-lactone (188 mg) and 2-phenylbutyric anhydride (310 mg) in d5 -pyridine (0.35 ml) was monitored by 1H n.m.r. until reaction was complete (1.5 hours). The mixture was dissolved in diethyl ether (20 ml), partitioned with aqueous hydrochloric acid (2×20 ml, 1M) and aqueous sodium hydroxide (2×10 ml, 1M). The combined alkaline extracts were acidified with 10M hydrochloric acid to pH 2, extracted with diethyl ether (2×10 ml) and the dried (MgSO4) ether extracts concentrated in vacuo to give (+)2-phenylbutyric acid (150 mg), [α]D25 +31° (c=1.0, benzene).

Provenance & Evidence