Reaction #2006418

Reaction equation

enone

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

MeOH

NMO

→

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

Solvents

THF

Conditions

Workup

1. 1
   OtherPurged with nitrogen
2. 2
   Filtrationfiltered through Celite
3. 3
   Otherremoved solvent
4. 4
   Otherby evaporation under vacuum
5. 5
   workup.ADDITIONwas added
6. 6
   workup.STIRRINGStirred at room temperature for 30 minutes
7. 7
   Filtrationfiltered through a plug of silica gel
8. 8
   OtherSolvent was evaporated under vacuum
9. 9
   Otherpurified by column chromatography

Procedure

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.

Source