Triphenylphosphine → 2-Heptanone, 1-(triphenylphosphoranylidene)-

HRID 2052324Notes

Reaction equation

HRID 2052324 reaction equation
Cl[CH2:2][C:3](=[O:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:10]1([P:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)(Cl)Cl>[C:3]([CH:2]=[P:16]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)(=[O:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 109536781-Chloroheptan-2-one

Product 1

HCID 107619442-Heptanone, 1-(triphenylphosphoranylidene)-Yield 20.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 1-chloroheptan-2-one (33 g.) and triphenylphosphine (60 g.) in chloroform (50 ml.) was saturated with nitrogen and refluxed under nitrogen overnight. The chloroform was removed in vacuo and the residue was dissolved in dichloromethane (150 ml.). Dry diethyl ether (600 ml.) was added to precipitate 2-oxoheptyltriphenylphosphonium chloride (60 g.), m.p. 165°-168° C. This compound (23 g.) was added portionwise to a solution of sodium carbonate (25 g.) in water (250 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. 40°-60° C.). The solid thus obtained was recrystallised from petroleum ether (b.p. 60°-80° C.) to give hexanoylmethylenetriphenylphosphorane (17 g.), m.p. 73°-74° C.

Workup

  1. temperaturerefluxed under nitrogen overnight
  2. customThe chloroform was removed in vacuo
  3. dissolutionthe residue was dissolved in dichloromethane (150 ml.)
  4. additionDry diethyl ether (600 ml.) was added to precipitate 2-oxoheptyltriphenylphosphonium chloride (60 g.), m.p. 165°-168° C
  5. additionThis compound (23 g.) was added portionwise to a solution of sodium carbonate (25 g.) in water (250 ml.)
  6. extractionThe solution was extracted with diethyl ether
  7. dry with materialthe ethereal extracts were dried over magnesium sulphate
  8. customThe solvent was removed by evaporation
  9. temperaturethe residue was cooled
  10. customtriturated with petroleum ether (b.p. 40°-60° C.)
  11. customThe solid thus obtained
  12. customwas recrystallised from petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-84da9cb300624eaf99fa679ba357c081
Source dataset
uspto-grants-1980_01
Patent number
US04183870

Reaction notes

Loading…