3-Methoxyphenol → HCID 22459131, compound

HRID 2185060Notes

Reaction equation

HRID 2185060 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-fde244b3c82142538094263b14d11c33
Source dataset
uspto-grants-2002_06
Patent number
US06399640B1

Reaction notes

Loading…