(E)-ethyl 3-(1-(3,4-difluorophenyl)cyclohexyl)acrylate → Ethyl 3-(1-(3,4-difluorophenyl)cyclohexyl)propanoate

HRID 71235Notes

Reaction equation

HRID 71235 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2(/[CH:15]=[CH:16]/[C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]>CO.[Pd]>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 1

HCID 86688201(E)-ethyl 3-(1-(3,4-difluorophenyl)cyclohexyl)acrylate

Product 1

HCID 66685623Ethyl 3-(1-(3,4-difluorophenyl)cyclohexyl)propanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (E)-ethyl 3-(1-(3,4-difluorophenyl)cyclohexyl)acrylate (550 mg, 1.869 mmol) in MeOH (20 mL) was added ˜150 mg of 10% Pd/C (wet, 50%), and the mixture was stirred under hydrogen (50 psi) for 6 hrs. The catalyst was removed by filtering through Celite and the solvent was evaporated off to give ethyl 3-(1-(3,4-difluorophenyl)cyclohexyl)propanoate as an oil. LC/MS: m/e 297.16 (M+H)+.

Workup

  1. customThe catalyst was removed
  2. filtrationby filtering through Celite
  3. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-1d2be606795e4de0a7bd0bc3b0b0c2e6
Source dataset
uspto-grants-2014_09
Patent number
US08822510B2

Reaction notes

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