Ethanol → Butanoic acid, 4-chloro-3-hydroxy-, ethyl ester

HRID 854140Notes

Reaction equation

HRID 854140 reaction equation
N[C:2]1[CH:7]=CN=CC=1.[CH2:8]([C@H:10]1[O:12][CH2:11]1)[Cl:9].[C]=[O:14].[CH2:15]([OH:17])C>>[CH2:7]([O:14][C:15](=[O:17])[CH2:11][CH:10]([OH:12])[CH2:8][Cl:9])[CH3:2]

Participants

5

Reactant 4

HCID 702EthanolHCID 17274-AminopyridineHCID 149428(+)-EpichlorohydrinHCID 178418416HCID 178418416, compound

Product 1

HCID 4377704Butanoic acid, 4-chloro-3-hydroxy-, ethyl esterYield 92%

Procedure

In a 50 mL-volumetric autoclave was added deaerated ethanol (10 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 30° C. for 30 hours. After cooling to room temperature, the solvent was removed in vacuo. The residue was subjected to Kugelrohr distillation to give 4-chloro-3-hydroxybutanoic acid ethyl ester (3.1 g, 92%, >99% ee) as a colorless oil. bp: 80° C./0.6 mmHg.

Workup

  1. additionwas introduced
  2. customthe mixture was reacted at 30° C. for 30 hours
  3. customthe solvent was removed in vacuo
  4. distillationThe residue was subjected to Kugelrohr distillation

Sources & evidence

ORD record
ord-1c389f08d34a4766ba4497cf2f93d91b
Source dataset
uspto-grants-2007_08
Patent number
US07256305B2

Reaction notes

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