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

HRID 1421397Notes

Reaction equation

HRID 1421397 reaction equation
[Cl:1][CH2:2][C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[H][H]>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

4

Reactant 2

HCID 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, 12.4 mg (0.008 mmol) of Ru2Cl4 ((R)-BIPHEMP)2NEt3 was 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, it was stirred for 2 hours at 100° C. After termination of the reaction, the conversion ratio, selectivity and optical purity were measured under the same chromatography conditions as in Example 5. At a conversion ratio of 95.5%, selectivity of 93.9% and optical purity of 95.7%ee, ethyl 4-chloro-(S)-3-hydroxybutyrate was obtained.

Workup

  1. additionwas charged
  2. customAfter termination of the reaction

Sources & evidence

ORD record
ord-1ed93c89947449039f6cb62c83e6e642
Source dataset
uspto-grants-2000_06
Patent number
US06075154

Reaction notes

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