Triphenylphosphine → 2-Methylhexanoylmethylenetriphenylphosphorane

HRID 372048Notes

Reaction equation

HRID 372048 reaction equation
Cl[CH2:2][C:3](=[O:10])[CH:4]([CH3:9])[CH2:5][CH2:6][CH2:7][CH3:8].[C:11]1([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)(Cl)Cl>[CH3:9][CH:4]([CH2:5][CH2:6][CH2:7][CH3:8])[C:3]([CH:2]=[P:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:10]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 205428901-Chloro-3-methylheptan-2-one

Product 1

HCID 205428842-MethylhexanoylmethylenetriphenylphosphoraneYield 29.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1-chloro-3-methylheptan-2-one (49.4 g.) and triphenylphosphine (79.5 g.) in chloroform (250 ml.) was saturated with nitrogen and refluxed under nitrogen overnight. The chloroform was removed in vacuo and the residue (crude 3-methyl-2-oxoheptyltriphenylphosphonium chloride) was added portionwise to a solution of sodium carbonate (109 g.) in water (1500 ml.) and the mixture was stirred vigorously for 24 hours. The solution was extracted with diethyl ether, and the ethereal extracts were dried over magnesium sulphate. The solvent was removed by evaporation and the residue was cooled and triturated with petroleum ether (b.p. 60°-80° C.) to give 2-methylhexanoylmethylenetriphenylphosphorane (35.2 g.), m.p. 107°-109° C.

Workup

  1. temperaturerefluxed under nitrogen overnight
  2. customThe chloroform was removed in vacuo
  3. additionthe residue (crude 3-methyl-2-oxoheptyltriphenylphosphonium chloride) was added portionwise to a solution of sodium carbonate (109 g.) in water (1500 ml.)
  4. extractionThe solution was extracted with diethyl ether
  5. dry with materialthe ethereal extracts were dried over magnesium sulphate
  6. customThe solvent was removed by evaporation
  7. temperaturethe residue was cooled
  8. customtriturated with petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-6a41da860a8e444499f7d8b3e68d3822
Source dataset
uspto-grants-1978_05
Patent number
US04088695

Reaction notes

Loading…