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

In a 50 mL-volumetric autoclave were added deaerated ethanol (10 mL), and thereto were added cobalt acetate tetrahydrate (250 mg, 1 mmol) and 10% Pd/C (10 mg). After covering the autoclave with a cap, carbon monoxide (1 MPa) and hydrogen gas (1 MPa) were introduced therein, successively and the mixture was reacted at 80° C. for 3 hours. After 3 hours the mixture was cooled to room temperature, and the mixed gas was emitted to give a solution containing dicobaltoctacarbonyl complex. Thereto were added 4-aminopyridine (47 mg, 0.5 mmol) and (S)-epichlorohydrin (1.8 g, 20 mmol, >99% ee). After covering the autoclave with a cap, carbon monoxide (1 MPa) was introduced therein and the mixture was reacted at 35° C. for 28 hours. After temperature of the mixture was made room temperature, the solvent was removed in vacuo. The residue was subjected to Kugelrohr distillation to give (S)-4-chloro-3- hydroxybutanoic acid ethyl ester (3.1 g, 92%, >99% ee) as a colorless oil.

1. additionwere introduced
2. customsuccessively and the mixture was reacted at 80° C. for 3 hours
3. customto give a solution
4. additioncontaining dicobaltoctacarbonyl complex
5. additionwas introduced
6. customthe mixture was reacted at 35° C. for 28 hours
7. customwas made room temperature
8. customthe solvent was removed in vacuo
9. distillationThe residue was subjected to Kugelrohr distillation

ORD record

ord-ce03cb5de30f4da7a7517cfa7311d7ef

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07256305B2