Ethyl 4-chloroacetoacetate → Ethyl (3S)-4-chloro-3-hydroxybutanoate

Participants

Reaction Steps

Into a 500-mL autoclave was introduced [{RuCl((R)-SEGPHOS)}2(μ-Cl)3][Me2NH2] (122 mg: 0.149 mmol). After the atmosphere in the autoclave was replaced with nitrogen, distilled ethanol (183 mL) and ethyl 4-chloroacetoacetate (60.9 g: 0.37 mol) were added thereto. The autoclave was heated until the temperature of the contents reached 90° C. and hydrogen (3.0 MPa) was forced into the autoclave to react the reaction mixture for 2 hours, during which the hydrogen pressure of 3.0 MPa was maintained. After completion of the reaction, the solvent was removed and the residue was distilled under reduced pressure to obtain ethyl (S)-4-chloro-3-hydroxybutanoate (54.6 g: yield, 88.5%).

Provenance & Evidence