Реакция #7457

Уравнение реакции

ammonium chloride

methyl 4-(diethylphosphorylmethyl)benzoate

sodium hydride

propionaldehyde

→

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

Растворители

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for 30 minutes
2. 2
   Экстракцияthe mixture was extracted with diethyl ether
3. 3
   ПромывкаThe organic layer was washed with water
4. 4
   Сушкаdried over anhydrous magnesium sulfate
5. 5
   Другоеthe solvent was removed under reduced pressure
6. 6
   ДругоеThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1)

Методика

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).

Источник