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

HRID 269430Notes

Reaction equation

HRID 269430 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-ff122a365446472fb84b624d7f45997d
Source dataset
uspto-grants-2008_11
Patent number
US07446229B2

Reaction notes

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