Triphenylphosphine → 3-Ethoxypropionylmethylenetriphenylphosphorane

HRID 259206ノート

反応式

HRID 259206 の反応式
Cl[CH2:2][C:3](=[O:9])[CH2:4][CH2:5][O: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>[CH2:7]([O:6][CH2:5][CH2:4][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])[CH3:8]

参加物

4

反応物 2

HCID 11776TriphenylphosphineHCID 140688891-Chloro-4-ethoxybutan-2-one

生成物 1

HCID 205429223-Ethoxypropionylmethylenetriphenylphosphorane収率 53.3%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A solution of 1-chloro-4-ethoxybutan-2-one (7.5 g.) and triphenylphosphine (13.5 g.) in chloroform (20 ml.) was saturated with nitrogen and heated at reflux under nitrogen overnight. The chloroform was removed in vacuo and the residue was dissolved in dichloromethane (35 ml.). Dry diethyl ether (300 ml.) was added to precipitate 4-ethoxy-2-oxobutyltriphenylphosphonium chloride (19 g.). This compound was added portionwise to a solution of sodium carbonate (10g.) in water (1000 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 3-ethoxypropionylmethylenetriphenylphosphorane (10.0 g.), m.p. 63°-65° C. Elemental analysis: found C, 76.6; H, 6.5; P, 8.2%; C24H25O2P requires: C, 76.6; H, 6.7;P 8.3%.

後処理

  1. temperatureheated
  2. temperatureat reflux under nitrogen overnight
  3. customThe chloroform was removed in vacuo
  4. dissolutionthe residue was dissolved in dichloromethane (35 ml.)
  5. additionDry diethyl ether (300 ml.) was added to precipitate 4-ethoxy-2-oxobutyltriphenylphosphonium chloride (19 g.)
  6. additionThis compound was added portionwise to a solution of sodium carbonate (10g.) in water (1000 ml.)
  7. extractionThe solution was extracted with diethyl ether
  8. dry with materialthe ethereal extracts were dried over magnesium sulphate
  9. customThe solvent was removed by evaporation
  10. temperaturethe residue was cooled
  11. customtriturated with petroleum ether (b.p. 60°-80° C.)

出典と根拠

ORDレコード
ord-8c5d8aed142748ad959f05a6a779aefe
出典データセット
uspto-grants-1977_07
特許番号
US04036872

反応ノート

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