Methanesulfonic Acid → Ethyl 4,4,4-trifluoro-3-hydroxybutanoate

HRID 381798

Reaction equation

HRID 381798 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3](=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].CS(O)(=O)=O.[H][H]>[Pt]>[F:1][C:2]([F:11])([F:12])[CH:3]([OH:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 178418361HCID 178418361, compound

Product 1

HCID 136210Ethyl 4,4,4-trifluoro-3-hydroxybutanoateYield 50.1%

Reagents, catalysts & solvents 1

HCID 23939PlatinumCatalyst

Conditions

Temperature
40 °C

Procedure

Ethyl 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 methanesulfonic acid (1.5 g, 2.9% 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, 25.3 g (50% yield) of ethyl 4,4,4-trifluoro-3-hydroxybutyrate is obtained.

Workup

  1. filtrationAfter filtration
  2. customto remove the catalyst

Sources & evidence

ORD record
ord-d5a853887b8d4c2fb460537e3b147d6c
Source dataset
uspto-grants-2001_10
Patent number
US06307094B1

Linked notes

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