Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Benzyl 3-(ethoxycarbonyl)-2-(2-methylpropyl)propenoate

HRID 745616

반응식

HRID 745616 반응식
[CH2:1]([O:3][C:4]([CH:6]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:5])[CH3:2].[CH3:26][CH:27]([CH3:41])[CH2:28][C:29](=O)[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]>ClCCl>[CH2:1]([O:3][C:4]([CH:6]=[C:29]([CH2:28][CH:27]([CH3:41])[CH3:26])[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])=[O:5])[CH3:2]

참가 물질

4

반응물 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 4072499Benzyl 4-methyl-2-oxopentanoate

생성물 1

HCID 53921709Benzyl 3-(ethoxycarbonyl)-2-(2-methylpropyl)propenoate수율 91.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
0 °C

실험 절차

Ethoxycarbonylmethylenetriphenylphosphorane (53.8 g., 0.155 mol.) was dissolved in dry dichloromethane (400 mls.) and the resulting solution was cooled to 0° C. To the cooled solution was added a solution of benzyl 4-methyl-2-oxopentanoate (34.0 g., 0.155 mol.) in dry dichloromethane (100 mls.) over a period of 25 minutes and the reaction mixture was then heated under reflux for 1 hour. The solvent was removed from the reaction mixture by evaporation in vacuo to yield an off-white solid. The solid was extracted with hexane (3×200 mls.) and the solvent was removed from the combined hexane extracts to yield a crude product as a yellow oil. The crude product was purified by distillation (0.6 mm Hg), to yield E and Z benzyl 3-(ethoxycarbonyl)-2-(2-methylpropyl)propenoate (41.0 g.) being collected at 137°-142° C.

후처리

  1. temperaturethe reaction mixture was then heated
  2. temperatureunder reflux for 1 hour
  3. customThe solvent was removed from the reaction mixture by evaporation in vacuo
  4. customto yield an off-white solid
  5. extractionThe solid was extracted with hexane (3×200 mls.)
  6. customthe solvent was removed from the combined hexane
  7. customto yield a crude product as a yellow oil
  8. distillationThe crude product was purified by distillation (0.6 mm Hg)

출처 및 근거

ORD 기록
ord-63285faa6da444b192971be90eb7537f
출처 데이터셋
uspto-grants-1986_07
특허 번호
US04599361

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