Menthol → 2-(Pyrrol-1-yl)malonic acid ethyl (-)-menthyl ester

HRID 256581

반응식

HRID 256581 반응식
[CH2:1]([O:3][C:4](=[O:16])[CH:5]([N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[CH:17]1([CH3:27])[CH2:22]C[CH:20]([CH:23](C)[CH3:24])[CH:19](O)[CH2:18]1>CCO.CCO.CCO.CCO.[Ti]>[CH:23]1([CH3:24])[CH2:20][CH2:19][CH:18]([CH:17]([CH3:27])[CH3:22])[CH:9]([O:8][C:6](=[O:7])[CH:5]([N:11]2[CH:12]=[CH:13][CH:14]=[CH:15]2)[C:4]([O:3][CH2:1][CH3:2])=[O:16])[CH2:10]1

참가 물질

4

반응물 2

HCID 1254MentholHCID 2782128diethyl 2-(1H-pyrrol-1-yl)malonate

생성물 1

HCID 538719252-(Pyrrol-1-yl)malonic acid ethyl (-)-menthyl ester수율 31.8%

시약·촉매·용매 1

HCID 2724286Titanium(IV)ethoxide촉매

반응 조건

온도
110 °C

실험 절차

To a mixture of 2-(pyrrol-1-yl)malonic acid diethyl ester (300.0 g) and (-)-menthol (417.0 g) was added tetraethyl titanate (10.0 g), and the resulting mixture was stirred at 110° C. for 19 hours. After removal of the (-)-menthol under reduced pressure, the residue was chromatographed on silica gel using n-hexane/ethyl acetate (50:1) as the eluent. Fractions containing the title compound were pooled and evaporated under reduced pressure to give the title compound (142.0 g, 31.8%) as a colorless oil.

후처리

  1. customAfter removal of the (-)-menthol under reduced pressure
  2. customthe residue was chromatographed on silica gel
  3. additionFractions containing the title compound
  4. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-f14a8b62c6884870a484f598b5c82ebb
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05258382

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