Methanol → Methyl (3S)-4-chloro-3-hydroxybutanoate

Participants

Reaction Steps

In a 50 mL-volumetric autoclave were added deaerated methanol (5 mL) and t-butanol (3 mL), and thereto were added 4-aminopyridine (47 mg, 0.5 mmol) and (S)-epichlorohydrin (1.9 g, 20 mmol, >99% ee). Then to the mixture was added crystalline dicobaltoctacarbonyl complex (171 mg, 0.5 mmol). After covering the autoclave with a cap, carbon monoxide (1 MPa) was introduced therein and the mixture was reacted at 40° C. for 5 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was subjected to Kugelrohr distillation to give (S)-4-chloro-3-hydroxybutanoic acid methyl ester (2.8 g, 92%, >99% ee) as a colorless oil.

Provenance & Evidence