Water → Methyl 4-(cyclopropylidenemethyl)benzoate

HRID 7356

反応式

HRID 7356 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 11600812Methyl 4-(cyclopropylidenemethyl)benzoate収率 69.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-b693a864a5f84c91904645550a8b9dac
出典データセット
uspto-grants-2006_08
特許番号
US07087579B2

関連ノート

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