3-Methoxyphenol → HCID 22459131, compound

HRID 1532174Notes

Reaction equation

HRID 1532174 reaction equation
Br[CH2:2][C:3](=[O:12])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=1)[O:21][CH2:2][C:3](=[O:12])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 90073-MethoxyphenolHCID 10796Cesium carbonateHCID 126080271-Bromo-4-phenylbutan-2-one

Product 1

HCID 22459131HCID 22459131, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A dry, DMF (80 mL) solution of the product of Example 63, Step B (5.519 grams) was exposed to 3-methoxyphenol (3.608 grams) followed by cesium carbonate (9.481 grams). After stirring at ambient temperature for 2 hours the reaction was partitioned between isopropyl acetate and pH4 pthalate buffer. The organic was washed twice with water, dried (magnesium sulfate) and filtered. Concentration and silica gel chromatography (5:1 hex/ethyl acetate) completed the isolation of the title compound, a yellow solid.

Workup

  1. customwas partitioned between isopropyl acetate and pH4
  2. washThe organic was washed twice with water
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationConcentration and silica gel chromatography (5:1 hex/ethyl acetate)

Sources & evidence

ORD record
ord-fea482e6f01446948de101777449c6c2
Source dataset
uspto-grants-2001_03
Patent number
US06200998B1

Reaction notes

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