반응 #8297

반응 방정식

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

용매

dichloromethane

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   온도The mixture is refluxed for 5 h
2. 2
   workup.STIRRINGstirred one hour
3. 3
   기타The organic layer is separated
4. 4
   세척washed with brine
5. 5
   건조dried over magnesium sulfate
6. 6
   여과The mixture is filtered
7. 7
   농축concentrated in vacuo
8. 8
   기타chromatographed on SiO2 (2% methanol/dichloromethane)

실험 절차

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.

출처