Reacción #7457

Ecuación de reacción

ammonium chloride

methyl 4-(diethylphosphorylmethyl)benzoate

sodium hydride

propionaldehyde

→

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

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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).

Fuente