(E)-methyl 4-(1-(4-fluorophenyl)cyclohexyl)but-3-enoate → Methyl 4-(1-(4-fluorophenyl)cyclohexyl)butanoate

HRID 1506298Notes

Reaction equation

HRID 1506298 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(/[CH:14]=[CH:15]/[CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1>CO.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 67168705(E)-methyl 4-(1-(4-fluorophenyl)cyclohexyl)but-3-enoate

Product 1

HCID 67168007Methyl 4-(1-(4-fluorophenyl)cyclohexyl)butanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (E)-methyl 4-(1-(4-fluorophenyl)cyclohexyl)but-3-enoate (Intermediate I-11C, 421 mg, 1.523 mmol) in methanol (20 mL) was added about 100 mg of 10% Pd on carbon (wet, 50%), and the mixture was stirred under hydrogen (50 psi) overnight. The catalyst was filtered off and the solvent was evaporated off to give the desired methyl 4-(1-(4-fluorophenyl)cyclohexyl)butanoate (quantitative yield) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 7.26 (2H, dd, J=8.91, 5.39 Hz), 7.00 (2H, t, J=8.80 Hz), 4.07 (2H, q, J=7.12 Hz), 2.12 (2H, t, J=7.37 Hz), 2.04 (2H, dd, J=13.42, 5.72 Hz), 1.24-1.63 (12H, m), 1.21 (3H, t, J=7.15 Hz).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-5482f8e1755d423d80625ea13ed0972d
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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