Triphenylphosphine → HCID 178445095, compound

HRID 2286067Notes

Reaction equation

HRID 2286067 reaction equation
Cl[CH2:2][C:3](=[O:9])[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[C:10]1([P:16](C2C=CC=CC=2)C2C=CC=CC=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(Cl)(Cl)Cl>[C:3]([CH:2]=[PH2:16][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=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 178445095HCID 178445095, compoundYield 34.4%

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 hexanoylmethylenephenylphosphorane (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-5994adb08f4147b9a6cd4ff73ee58a80
Source dataset
uspto-grants-1982_04
Patent number
US04325967

Reaction notes

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