Methyl 2-[3,5-Bis(trifluoromethyl)phenyl]-2-propenoate → (RS)-Methyl alpha-Methyl-3,5-bis(trifluoromethyl)benzeneacetate

HRID 2212991Notes

Reaction equation

HRID 2212991 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:13](=[CH2:18])[C:14]([O:16][CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1>[Pd].C(O)C>[CH3:18][CH:13]([C:5]1[CH:6]=[C:7]([C:9]([F:10])([F:12])[F:11])[CH:8]=[C:3]([C:2]([F:1])([F:19])[F:20])[CH:4]=1)[C:14]([O:16][CH3:17])=[O:15]

Participants

4

Reactant 1

HCID 21955189Methyl 2-[3,5-Bis(trifluoromethyl)phenyl]-2-propenoate

Product 1

HCID 21955130(RS)-Methyl alpha-Methyl-3,5-bis(trifluoromethyl)benzeneacetateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

An aqueous slurry of palladium on carbon (50 mg) was added to a solution of methyl 2-[3,5-bis(trifluoromethyl)phenyl]-2-propenoate (Description 2, 1.0 g, 3.4 mmol) in ethanol (40 mL) and the mixture was shaken under an atmosphere of hydrogen (50 psi) for 1 hour. The mixture was filtered and the solvent was evaporated under reduced pressure to give the title compound as a colorless oil (0.97 g, 95%). 1H NMR (360 MHz, CDCl3) δ 1.57 (3H, d, J 7.2 Hz), 3.71 (3H, s), 3.86 (1H, q, J 7.2 Hz), 7.76 (2H, s) and 7.79 (1H, s).

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b2be84c6b03a402d86ea5780ce6bd563
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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