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

HRID 1181646Notes

Reaction equation

HRID 1181646 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-f3a63d2f20b243419a46b58aed1b3943
Source dataset
uspto-grants-2007_10
Patent number
US07285683B2

Reaction notes

Loading…