2-(4-benzyloxy-3,5-dimethoxy-phenyl)-1-(2,2-dimethyl-2H-chromen-6-yl)-ethanone → 1-(2,2-Dimethyl-chroman-6-yl)-2-(4-hydroxy-3,5-dimethoxy-phenyl]-ethanone

HRID 1724001Notes

Reaction equation

HRID 1724001 reaction equation
C([O:8][C:9]1[C:14]([O:15][CH3:16])=[CH:13][C:12]([CH2:17][C:18]([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[O:26][C:25]([CH3:31])([CH3:30])[CH:24]=[CH:23]3)=[O:19])=[CH:11][C:10]=1[O:32][CH3:33])C1C=CC=CC=1>CO.[Pd]>[CH3:30][C:25]1([CH3:31])[CH2:24][CH2:23][C:22]2[C:27](=[CH:28][CH:29]=[C:20]([C:18](=[O:19])[CH2:17][C:12]3[CH:13]=[C:14]([O:15][CH3:16])[C:9]([OH:8])=[C:10]([O:32][CH3:33])[CH:11]=3)[CH:21]=2)[O:26]1

Participants

4

Reactant 1

HCID 575584302-(4-benzyloxy-3,5-dimethoxy-phenyl)-1-(2,2-dimethyl-2H-chromen-6-yl)-ethanone

Product 1

HCID 575584351-(2,2-Dimethyl-chroman-6-yl)-2-(4-hydroxy-3,5-dimethoxy-phenyl]-ethanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(4-benzyloxy-3,5-dimethoxy-phenyl)-1-(2,2-dimethyl-2H-chromen-6-yl)-ethanone (62.8 mg) dissolved in methanol (5.0 mL) and hexanes (3.3 mL) was added palladium on carbon (19.13 mg, 10% on carbon). The reaction mixture was purged with nitrogen numerous times before being exposed to a hydrogen atmosphere. Hydrogenation proceeded at room temperature and at atmospheric pressure. After 15 minutes, the reaction was purged again with nitrogen and the reaction mixture was filtered to remove the catalyst. The filtrate was concentrated to yield the desired product.

Workup

  1. customThe reaction mixture was purged with nitrogen numerous times
  2. customproceeded at room temperature and at atmospheric pressure
  3. customthe reaction was purged again with nitrogen
  4. filtrationthe reaction mixture was filtered
  5. customto remove the catalyst
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-89962ecfa2d34c86b41adc8cefedbba0
Source dataset
uspto-grants-2009_02
Patent number
US07485283B2

Reaction notes

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