تفاعل #7457

معادلة التفاعل

ammonium chloride

methyl 4-(diethylphosphorylmethyl)benzoate

sodium hydride

propionaldehyde

→

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

المذيبات

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر