反応 #7457

反応方程式

ammonium chloride

methyl 4-(diethylphosphorylmethyl)benzoate

sodium hydride

propionaldehyde

→

methyl (E)-4-(but-1-en-1-yl)benzoate

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 30 minutes
2. 2
   抽出the mixture was extracted with diethyl ether
3. 3
   洗浄The organic layer was washed with water
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/ethyl acetate=5/1)

実験手順

To a suspension of sodium hydride (60%, 0.97 g) in tetrahydrofuran (80 mL) was added methyl 4-(diethylphosphorylmethyl)benzoate (5.8 g) at 0° C., and the mixture was stirred for 30 minutes. To the reaction mixture was added a solution of propionaldehyde (1.6 mL) in tetrahydrofuran (10 mL), and the mixture was stirred at room temperature for 30 minutes. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with diethyl ether. The organic layer was washed with water 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/ethyl acetate=5/1) to give methyl (E)-4-(but-1-en-1-yl)benzoate (2.5 g).

出典