(E)-4-(1-(4-fluorophenyl)cyclohexyl)but-3-enoic acid → 4-(1-(4-Fluorophenyl)cyclohexyl)butanoic acid

HRID 714247Notes

Reaction equation

HRID 714247 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2(/[CH:14]=[CH:15]/[CH2:16][C:17]([OH:19])=[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]([OH:19])=[O:18])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 66685187(E)-4-(1-(4-fluorophenyl)cyclohexyl)but-3-enoic acid

Product 1

HCID 666855454-(1-(4-Fluorophenyl)cyclohexyl)butanoic acidYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (E)-4-(1-(4-fluorophenyl)cyclohexyl)but-3-enoic acid (37.3 mg, 0.142 mmol) in MeOH (10 mL) was added about 50 mg of 10% Pd/C (50% wet) and the solution was stirred under H2 (50 psi) for 4 hrs. After removal of the catalyst by filtering thru Celite, the solvent was evaporated off to give 4-(1-(4-fluorophenyl)cyclohexyl)butanoic acid (30 mg, 0.113 mmol, 80% yield) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 9.80 (1 H, br. s.), 7.42-7.49 (1 H, m), 7.21-7.27 (2 H, m), 6.98 (2 H, t, J=8.79 Hz), 2.11 (2 H, t, J=7.47 Hz), 1.97-2.07 (2 H, m), 1.17-1.61 (10 H, m).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtering thru Celite
  3. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-4f169f5a34d84e0e9dc3d10cfac673e0
Source dataset
uspto-grants-2015_11
Patent number
US09187437B2

Reaction notes

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