4-Chlorophenol → tert-butyl (2R)-(+)-2-(4'-chlorophenoxy)propionate

Participants

Reaction Steps

To a stirred solution of known tert-butyl L-(+)-lactate (217 mg), 4-chlorophenol (219 μl) and triphenylphosphine (584 mg) in dry tetrahydrofuran (8 ml) on an ice bath, diethylazodicarboxylate (350 μl) was added dropwise over about 10 minutes. After the addition, the ice bath was removed and the mixture was further stirred at room temperatures for 24 hours. The reaction mixture was evaporated with a rotary evaporator (water bath temperaure 38° C.). The residue thus obtained was purified by silica gel chromatography [silica gel 50 g, eluant:ethyl acetate-hexane (1:10)] to give tert-butyl (2R)-(+)-2-(4'-chlorophenoxy)propionate (256 mg).

Provenance & Evidence