Ethyl 3-(4-benzyloxy-3-cyclopentyl-phenyl)prop-2-enoate → Ethyl 3-(3-cyclopentyl-4-hydroxy-phenyl)propanoate

HRID 471950Notes

Reaction equation

HRID 471950 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[CH:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][C:10]=1[CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1)C1C=CC=CC=1>C(O)C.[Pd]>[CH:22]1([C:10]2[CH:11]=[C:12]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:13]=[CH:14][C:9]=2[OH:8])[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

4

Reactant 1

HCID 67455985Ethyl 3-(4-benzyloxy-3-cyclopentyl-phenyl)prop-2-enoate

Product 1

HCID 59394986Ethyl 3-(3-cyclopentyl-4-hydroxy-phenyl)propanoateYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A flask containing 10% Pd/C (120 mg) was evacuated and then purged under a N2 atmosphere. To this was added a solution of ethyl 3-(4-benzyloxy-3-cyclopentyl-phenyl)prop-2-enoate (1.2 g, 3.42 mmol) in ethanol (15 mL). The reaction was stirred under H2 atmosphere for 12 h at room temperature. The catalyst was filtered off and the solvent was removed under reduced pressure. Purification by silica gel chromatography (0-30% ethyl acetate/hexanes) afforded ethyl 3-(3-cyclopentyl-4-hydroxy-phenyl)propanoate (857 mg, 96% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 9.01 (s, 1H), 6.93 (d, J=2.1 Hz, 1H), 6.79 (dd, J=2.2, 8.1 Hz, 1H), 6.65 (d, J=8.1 Hz, 1H), 4.02 (q, J=7.1 Hz, 2H), 3.21-3.12 (m, 1H), 2.71 (t, J=7.5 Hz, 2H), 2.53-2.50 (m, obscured by DMSO peak, 2H), 1.92-1.85 (m, 2H), 1.78-1.68 (m, 2H), 1.66-1.55 (m, 2H), 1.54-1.45 (m, 2H), 1.15 (t, J=7.1 Hz, 3H).

Workup

  1. customwas evacuated
  2. custompurged under a N2 atmosphere
  3. filtrationThe catalyst was filtered off
  4. customthe solvent was removed under reduced pressure
  5. customPurification by silica gel chromatography (0-30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-dc7ec00cec3a40ddb3d45f7141bf6063
Source dataset
uspto-grants-2014_01
Patent number
US08633189B2

Reaction notes

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