Reaktion #8297

Reaktionsgleichung

sodium hydroxide

Trimethylaluminum

benzophenone hydrazone

4-(3-methoxy-phenyl)-dihydro-furan-2-one

→

title compound

4-Hydroxy-3-(3-methoxy-phenyl)-butyric acid benzhydrylidene-hydrazide

Lösungsmittel

dichloromethane

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture is refluxed for 5 h
2. 2
   workup.STIRRINGstirred one hour
3. 3
   SonstigeThe organic layer is separated
4. 4
   Waschenwashed with brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   FiltrationThe mixture is filtered
7. 7
   Einengenconcentrated in vacuo
8. 8
   Sonstigechromatographed on SiO2 (2% methanol/dichloromethane)

Vorschrift

Trimethylaluminum (12 mL, 2 M in hexane, 24 mmol) is added dropwise to a solution of benzophenone hydrazone (1.57 g, 8 mmol) in dichloromethane (20 mL) at room temperature and under nitrogen. After the mixture is stirred for 30 min, 4-(3-methoxy-phenyl)-dihydro-furan-2-one, (1.54 g, 8 mmol) in dichloromethane (5 mL) is added. The mixture is refluxed for 5 h cooled to room temperature and diluted with dichloromethane (30 mL). The mixture is treated with 4 N sodium hydroxide (30 mL) and stirred one hour. The organic layer is separated, washed with brine and, dried over magnesium sulfate. The mixture is filtered, concentrated in vacuo and chromatographed on SiO2 (2% methanol/dichloromethane) to yield the title compound, 2.25 g (73%) as a pale yellow oil.

Quelle