Acetaldehyde → 6-Chloro-α-methyl-5-(phenylmethoxy)-2-pyridinemethanol

Participants

Reaction Conditions

Reaction Steps

2-Chloro-3-benzyloxy-6-iodo-pyridine (416 mg, 1.2 mmol) in THF (4 mL) was cooled to -78° C. and treated with n-butyllithium (1.2 mL of 1.6M in hexanes, 1.92 mmol). After 60 minutes, acetaldehyde (237 mg, 5.4 mmol) was added and the reaction was allowed to warm to 22° C. over 2 hours. The reaction was quenched with water (5 mL) and concentrated in vacuo. The remaining solution was extracted several times with ethyl acetate, dried over MgSO4, and concentrated in vacuo to yield an oil. The oil was chromatographed 1:1 hexane/ethyl acetate to yield 220 mg (70%) of 2-chloro-3-benzyloxy-6-(1-hydroxyethyl)-pyridine.

Provenance & Evidence