Reaktion #7452

Reaktionsgleichung

Water

cyclopropyltriphenylphosphonium bromide

sodium hydride

methyl terephthalaldehydate

→

methyl 4-(cyclopropylidenemethyl)benzoate

Ausbeute 69.8%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at 70° C. for 7 days
2. 2
   Extraktionthe mixture was extracted with diethyl ether
3. 3
   WaschenThe organic layer was washed with water and brine
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   Sonstigethe solvent was removed under reduced pressure
6. 6
   SonstigeThe residue was purified by column chromatography on silica gel (eluent: hexane/dichloromethane=1/1)

Vorschrift

To a suspension of sodium hydride (60%, 0.27 g) in tetrahydrofuran (40 mL) was added cyclopropyltriphenylphosphonium bromide (2.6 g), and the mixture was stirred at 70° C. for 2 hours. To the reaction mixture was added methyl terephthalaldehydate (1.0 g), and the mixture was stirred at 70° C. for 7 days. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The organic layer was washed with water and brine, 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/dichloromethane=1/1) to give methyl 4-(cyclopropylidenemethyl)benzoate (0.80 g).

Quelle