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

HRID 269429Notes

Reaction equation

HRID 269429 reaction equation
[CH2:1]([CH:5]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:2][CH2:3][CH3:4].[CH3:25][O:26][C:27]1[CH:28]=[C:29]([C:35]2([CH:40]=O)[CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:30]=[C:31]([O:33][CH3:34])[CH:32]=1>C1COCC1>[CH3:34][O:33][C:31]1[CH:30]=[C:29]([C:35]2([CH:40]=[CH:5][CH2:1][CH2:2][CH2:3][CH3:4])[CH2:36][CH2:37][CH2:38][CH2:39]2)[CH:28]=[C:27]([O:26][CH3:25])[CH:32]=1

Participants

4

Reactant 2

HCID 10980496(Butylmethylene)triphenylphosphoraneHCID 22066297(3,5-Dimethoxyphenyl)cyclopentane carboxaldehyde

Product 1

HCID 692046641-(3,5-Dimethoxyphenyl)-1-(hex-1-enyl)-cyclopentaneYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the above slurry of (butylmethylene)triphenylphosphorane at 10° C. under an argon atmosphere was added dropwise a solution of (3,5-dimethoxyphenyl)cyclopentane carboxaldehyde (1 equiv.) in dry THF (0.21M). The reaction was stirred for 45 min and upon completion was quenched by the addition of saturated aqueous ammonium chloride. The organic layer was separated and the aqueous phase was extracted twice with diethyl ether. The combined organic layer was washed with brine, dried over MgSO4 and the solvent was evaporated under reduced pressure to give an oil. The crude product was purified through a short column of silica gel using 5% diethyl ether-petroleum ether as eluent to afford the title compound in 96% yield.

Workup

  1. customwas quenched by the addition of saturated aqueous ammonium chloride
  2. customThe organic layer was separated
  3. extractionthe aqueous phase was extracted twice with diethyl ether
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. customthe solvent was evaporated under reduced pressure
  7. customto give an oil
  8. customThe crude product was purified through a short column of silica gel using 5% diethyl ether-petroleum ether as eluent

Sources & evidence

ORD record
ord-18189b9ca3df4693a9938cea99dc7a96
Source dataset
uspto-grants-2008_11
Patent number
US07446229B2

Reaction notes

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