反应 #2006418

反应方程式

enone

Methyl-4-(3-oxo-3-phenylpropenyl)-benzoate

MeOH

NMO

→

Methyl-4-(3-oxo-3-phenylpropyl)-benzoate

溶剂

THF

反应条件

后处理

1. 1
   其他Purged with nitrogen
2. 2
   过滤filtered through Celite
3. 3
   其他removed solvent
4. 4
   其他by evaporation under vacuum
5. 5
   workup.ADDITIONwas added
6. 6
   workup.STIRRINGStirred at room temperature for 30 minutes
7. 7
   过滤filtered through a plug of silica gel
8. 8
   其他Solvent was evaporated under vacuum
9. 9
   其他purified by column chromatography

实验过程

The aromatic enone 46 (321 mg, 1.20 mmol) was dissolved in anhydrous THF (6 mL) and anhydrous MeOH (6 ml). Added 2 small scoops of Pd 10% on activated C, placed under an atmosphere of hydrogen and allowed to stir for 2 hours at room temperature. Purged with nitrogen, filtered through Celite and removed solvent by evaporation under vacuum. The benzylic alcohol is reoxidized to the ketone by the following procedure. The crude was taken back in anhydrous CH2Cl2 (10 mL), with 3 Å molecular sieves, TPAP (1 scoop) was added followed by NMO (212 mg, 1.8 mmol). Stirred at room temperature for 30 minutes and filtered through a plug of silica gel. Solvent was evaporated under vacuum and purified by column chromatography using 10% EtOAc/Hexane.

来源