Ethyl 2-methyl-4,4,4-trifluoroacetoacetate → Ethyl 3-hydroxy-2-methyl-4,4,4-trifluorobutyrate

HRID 381797Notes

Reaction equation

HRID 381797 reaction equation
[CH3:1][CH:2]([C:8]([C:10]([F:13])([F:12])[F:11])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[H][H]>[Pt].C(N(CC)CC)C>[CH3:1][CH:2]([CH:8]([OH:9])[C:10]([F:13])([F:11])[F:12])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 2

HCID 2737204Ethyl 2-methyl-4,4,4-trifluoroacetoacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 533787Ethyl 3-hydroxy-2-methyl-4,4,4-trifluorobutyrateYield 96%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
40 °C

Procedure

Ethyl 2-methyl-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 ethyl 2-methyl-4,4,4-trifluoro-3-hydroxybutyrate is obtained.

Workup

  1. filtrationAfter filtration
  2. customto remove the catalyst

Sources & evidence

ORD record
ord-18e99ffb26774e509b424843c2cef869
Source dataset
uspto-grants-2001_10
Patent number
US06307094B1

Reaction notes

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