Isopropyl 4,4,4-Trifluoroacetoacetate → Isopropyl 4,4,4-trifluoro-3-hydroxybutyrate

HRID 381801Notes

Reaction equation

HRID 381801 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3](=[O:11])[CH2:4][C:5]([O:7][CH:8]([CH3:10])[CH3:9])=[O:6].[H][H]>[Pt].C(N(CC)CC)C>[F:1][C:2]([F:12])([F:13])[CH:3]([OH:11])[CH2:4][C:5]([O:7][CH:8]([CH3:10])[CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 586897Isopropyl 4,4,4-TrifluoroacetoacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 10313549Isopropyl 4,4,4-trifluoro-3-hydroxybutyrateYield 96%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
40 °C

Procedure

Isopropyl 4,4,4-trifluoroacetoacetate (50 g), under a blanket of nitrogen gas, is heated to 40° C. and treated with platinum (0.1 g of 5% Pt/C, 0.01% load) and triethylamine (0.2 g, 0.4 % load). Hydrogen is charged to a pressure of 5 bars, and the mixture agitated at 40° C. for 6h. After filtration to remove the catalyst, 48.5 g (96% yield) of isopropyl 4,4,4-trifluoro-3-hydroxybutyrate is obtained.

Workup

  1. filtrationAfter filtration
  2. customto remove the catalyst

Sources & evidence

ORD record
ord-c20e36c0a4c2410186d99a797f0d059c
Source dataset
uspto-grants-2001_10
Patent number
US06307094B1

Reaction notes

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