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

HRID 372054ノート

反応式

HRID 372054 の反応式
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]

参加物

4

反応物 2

HCID 11776TriphenylphosphineHCID 109536781-Chloroheptan-2-one

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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.

後処理

  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.)

出典と根拠

ORDレコード
ord-0e33deae2dd042c692b25adb89556246
出典データセット
uspto-grants-1978_05
特許番号
US04088695

反応ノート

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