Triethylamine → 4-Chloro-3-hydroxybutyric acid ethyl ester, (3R)-

HRID 2186496Notes

Reaction equation

HRID 2186496 reaction equation
[Cl:1][CH2:2][C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].CCN(CC)CC>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 8471TriethylamineHCID 69484Ethyl 4-chloroacetoacetate

Product 1

HCID 27344454-Chloro-3-hydroxybutyric acid ethyl ester, (3R)-Yield 75.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 200 ml autoclave were charged 40.0 g (0.24 mol) of ethyl 4-chloro-3-oxobutyrate, 20 mg of Ru2Cl4((S)-Tol-BINAP)2.NEt3, and 40 ml of ethanol, and reaction was conducted at 100° C. under a hydrogen pressure of 300 KPa for 5 hours. After the solvent was removed, the reaction mixture was distilled (60° C./200 Pa.) to give 30.3 g of the title compound. Optical purity: 95%e.e.

Workup

  1. customwas conducted at 100° C. under a hydrogen
  2. customfor 5 hours
  3. customAfter the solvent was removed
  4. distillationthe reaction mixture was distilled (60° C./200 Pa.)

Sources & evidence

ORD record
ord-f926246196d742d7ad272e780466746f
Source dataset
uspto-grants-2002_06
Patent number
US06403804B1

Reaction notes

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