Water → Methyl 4-(cyclopropylidenemethyl)benzoate

HRID 7356

반응식

HRID 7356 반응식
[H-].[Na+].[Br-].[CH:4]1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:6][CH2:5]1.[CH3:26][O:27][C:28]([C:30]1[CH:35]=[CH:34][C:33]([CH:36]=O)=[CH:32][CH:31]=1)=[O:29].O>O1CCCC1>[C:4]1(=[CH:36][C:33]2[CH:34]=[CH:35][C:30]([C:28]([O:27][CH3:26])=[O:29])=[CH:31][CH:32]=2)[CH2:6][CH2:5]1

참가 물질

6

반응물 4

HCID 962WaterHCID 15294Methyl 4-FormylbenzoateHCID 24758Sodium hydrideHCID 2723931Cyclopropyltriphenylphosphonium bromide

생성물 1

HCID 11600812Methyl 4-(cyclopropylidenemethyl)benzoate수율 69.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

To a suspension of sodium hydride (60%, 0.27 g) in tetrahydrofuran (40 mL) was added cyclopropyltriphenylphosphonium bromide (2.6 g), and the mixture was stirred at 70° C. for 2 hours. To the reaction mixture was added methyl terephthalaldehydate (1.0 g), and the mixture was stirred at 70° C. for 7 days. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/dichloromethane=1/1) to give methyl 4-(cyclopropylidenemethyl)benzoate (0.80 g).

후처리

  1. stirringthe mixture was stirred at 70° C. for 7 days
  2. extractionthe mixture was extracted with diethyl ether
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: hexane/dichloromethane=1/1)

출처 및 근거

ORD 기록
ord-b693a864a5f84c91904645550a8b9dac
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087579B2

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