Triphenylphosphine → 3-Ethoxypropionylmethylenetriphenylphosphorane

HRID 259206노트

반응식

HRID 259206 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

HCID 205429223-Ethoxypropionylmethylenetriphenylphosphorane수율 53.3%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

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%.

후처리

  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.)

출처 및 근거

ORD 기록
ord-8c5d8aed142748ad959f05a6a779aefe
출처 데이터셋
uspto-grants-1977_07
특허 번호
US04036872

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