反応 #7452

反応方程式

Water

cyclopropyltriphenylphosphonium bromide

sodium hydride

methyl terephthalaldehydate

→

methyl 4-(cyclopropylidenemethyl)benzoate

収率 69.8%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred at 70° C. for 7 days
2. 2
   抽出the mixture was extracted with diethyl ether
3. 3
   洗浄The organic layer was washed with water and brine
4. 4
   乾燥dried over anhydrous magnesium sulfate
5. 5
   その他the solvent was removed under reduced pressure
6. 6
   その他The residue was purified by column chromatography on silica gel (eluent: hexane/dichloromethane=1/1)

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).

出典