반응 #7457

반응 방정식

ammonium chloride

methyl 4-(diethylphosphorylmethyl)benzoate

sodium hydride

propionaldehyde

→

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

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

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

실험 절차

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).

출처