Ethyl 4-chloroacetoacetate → 4-Chloro-3-hydroxybutyric acid ethyl ester, (3R)-
Reaction equation
[Cl:1][CH2:2][C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]>C(O)C>[Cl:1][CH2:2][C@H:3]([OH:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
100 g of ethyl 4-chloro-3-oxobutyrate and 64.9 mg of {[Ru (p-cymene) I (+) TMBTP] I}, prepared in example 1, are placed under argon in a 3-liter reactor, in 1000 ml of ethyl alcohol degassed with argon; the mixture is heated at 120° C. under argon and pressurised with hydrogen at 5 bar. After 3 h, the mixture is cooled, concentrated at reduced pressure, and the residue distilled with 5 mm Hg vacuum. 91 g of ethyl (+) (R)-4-chloro-3-hydroxybutyrate are obtained with an e.e. of 97% by gas-chromatography analysis.
Workup
- customprepared in example 1
- customdegassed with argon
- temperaturethe mixture is cooled
- concentrationconcentrated at reduced pressure
- distillationthe residue distilled with 5 mm Hg vacuum
Sources & evidence
- ORD record
- ord-0a8ac851da3b43fd95dbb90f5859c41e
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06566552B2
Reaction notes
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