Methanol → HCID 18618679, compound

HRID 1919236Notes

Reaction equation

HRID 1919236 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:6][CH:5]=1.CO.C[N+]1([O-])CCOCC1>C1COCC1.[Pd]>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12](=[O:19])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 82029Methyl morpholine oxideHCID 610239HCID 610239, compound

Product 1

HCID 18618679HCID 18618679, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

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.

Workup

  1. customPurged with nitrogen
  2. filtrationfiltered through Celite
  3. customremoved solvent
  4. customby evaporation under vacuum
  5. additionwas added
  6. stirringStirred at room temperature for 30 minutes
  7. filtrationfiltered through a plug of silica gel
  8. customSolvent was evaporated under vacuum
  9. custompurified by column chromatography

Sources & evidence

ORD record
ord-88d8d448171c476ca5c56d2592b2845b
Source dataset
uspto-grants-2012_05
Patent number
USRE043343E1

Reaction notes

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