tert-Butanol → t-butyl (S)-(-)-4-chloro-3-hydroxybutyrate

HRID 1647333Notes

Reaction equation

HRID 1647333 reaction equation
[Cl:1][CH2:2][C:3](=[O:12])[CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C(O)(C)(C)C>C(Cl)Cl>[Cl:1][CH2:2][C@@H:3]([OH:12])[CH2:4][C:5]([O:7][C:8]([CH3:10])([CH3:9])[CH3:11])=[O:6]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 2724514tert-Butyl 4-chloro-3-oxobutyrate

Product 1

HCID 53817676t-butyl (S)-(-)-4-chloro-3-hydroxybutyrateYield 90.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

In a 100 ml Hastelloy-made autoclave having been purged with nitrogen were charged 58.35 g (0.3 mol) of t-butyl 4-chloroacetoacetate and 120 ml of t-butyl alcohol, and solution of 250 mg (0,00015 mol) of Ru2Cl4 [(R)-(+)-BINAP]2Et3N in 2 ml of methylene chloride was added thereto. The mixture was stirred at 100° C. under a hydrogen pressure of 10 to 15 kg/cm2 for 2 hours to conduct hydrogenation, The solvent was evaporated, and the residue was distilled under reduced pressure to give 53.0 g (percent yield: 90%) of t-butyl (S)-(-)-4-chloro-3-hydroxybutyrate as a colorless clear liquid.

Workup

  1. customhaving been purged with nitrogen
  2. additionwas added
  3. customThe solvent was evaporated
  4. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-eec759b49b474437a7cce417e3431b76
Source dataset
uspto-grants-1995_07
Patent number
US05430171

Reaction notes

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