Sodium Carbonate → Ethyl (3S)-4-chloro-3-hydroxybutanoate

HRID 1421396Notes

Reaction equation

HRID 1421396 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[Cl:7][CH2:8][C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].[H][H]>C(O)C>[Cl:7][CH2:8][C@@H:9]([OH:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 69484Ethyl 4-chloroacetoacetateHCID 178418361HCID 178418361, compound2×

Product 1

HCID 7019277Ethyl (3S)-4-chloro-3-hydroxybutanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a stainless steel autoclave, 21 mg of sodium carbonate and 14.1 mg (0.008 mmol) of Ru2Cl4 ((-)-BIFLUP)2NEt3 were charged, and the air in the autoclave was replaced with nitrogen. Further, 6.6 ml of ethanol and 2.7 ml (20 mmol) of ethyl 4-chloroacetoacetate were added, and the nitrogen in the autoclave was replaced with hydrogen. At a hydrogen pressure of 10 kgf/cm2, the solution was stirred for 2 hours at 100° C. After termination of the reaction, the conversion ratio, selectivity and optical purity were measured by gas chromatography and liquid chromatography. At a conversion ratio of 100%, selectivity of 96.3% and optical purity of 96.8%ee, ethyl 4-chloro-(S)-3-hydroxybutyrate was obtained.

Workup

  1. customAfter termination of the reaction

Sources & evidence

ORD record
ord-1f87aa65c2294f169245dae8a4040759
Source dataset
uspto-grants-2000_06
Patent number
US06075154

Reaction notes

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