Reaction #7457

Reaction equation

ammonium chloride

methyl 4-(diethylphosphorylmethyl)benzoate

sodium hydride

propionaldehyde

→

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

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

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

Procedure

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).

Source