1-(3,5-Dimethoxyphenyl)-1-(hex-1-enyl)-cyclopentane → 1-(3,5-Dimethoxyphenyl)-1-hexyl-cyclopentane

HRID 1181647Notes

Reaction equation

HRID 1181647 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1>C(OCC)(=O)C.[Pd]>[CH3:10][O:9][C:7]1[CH:6]=[C:5]([C:11]2([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

4

Reactant 1

HCID 692046641-(3,5-Dimethoxyphenyl)-1-(hex-1-enyl)-cyclopentane

Product 1

HCID 220662791-(3,5-Dimethoxyphenyl)-1-hexyl-cyclopentaneYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(3,5-dimethoxyphenyl)-1-(hex-1-enyl)-cyclopentane (1 equiv.) in ethyl acetate (0.11M) was added 10% Pd/C (17%, w/w) and the resulting suspension was stirred vigorously under an hydrogen atmosphere, overnight at room temperature. The catalyst was removed by filtration through celite and the filtrate was evaporated under reduced pressure to afford the crude product. Purification through a short column of silica gel using 5% diethyl ether-petroleum ether yielded the title compound in 95% yield.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. customthe filtrate was evaporated under reduced pressure
  3. customto afford the crude product
  4. customPurification through a short column of silica gel using 5% diethyl ether-petroleum ether

Sources & evidence

ORD record
ord-edfef51c75824de5b0fcbcd9c494c67c
Source dataset
uspto-grants-2007_10
Patent number
US07285683B2

Reaction notes

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