4,4,4-Trifluoro-2-(2,2,2-trifluoroethyl)but-2-enoic acid ethyl ester → 4,4,4-Trifluoro-2-(2,2,2-trifluoroethyl)-butyric acid ethyl ester

HRID 1594312Notes

Reaction equation

HRID 1594312 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]([CH2:11][C:12]([F:15])([F:14])[F:13])=[CH:6][C:7]([F:10])([F:9])[F:8])[CH3:2]>C1COCC1.[Pd]>[CH2:1]([O:3][C:4](=[O:16])[CH:5]([CH2:11][C:12]([F:13])([F:14])[F:15])[CH2:6][C:7]([F:8])([F:10])[F:9])[CH3:2]

Participants

4

Reactant 1

HCID 744100564,4,4-Trifluoro-2-(2,2,2-trifluoroethyl)but-2-enoic acid ethyl ester

Product 1

HCID 445414254,4,4-Trifluoro-2-(2,2,2-trifluoroethyl)-butyric acid ethyl esterYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4,4,4-Trifluoro-2-(2,2,2-trifluoroethyl)-but-2-enoic acid ethyl ester (5.0 g, 20.0 mmol) in THF (20 mL) was treated with Pd/C (2.5 g, 5%), and H2 (1 atm.) at 25° C. for 17 h. The reaction mixture was filtered through a pad of the Celiteg reagent, rinsed with Et2O (50 mL) and the filtrate was distilled to remove Et2O and THF to afford the product as colorless liquid (5.0 g, 99%).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of the Celiteg reagent
  2. washrinsed with Et2O (50 mL)
  3. distillationthe filtrate was distilled
  4. customto remove Et2O and THF

Sources & evidence

ORD record
ord-df09ab2fe30a4ba0b3e7272682211410
Source dataset
uspto-grants-2007_11
Patent number
US07300951B2

Reaction notes

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