Cesium carbonate → HCID 22459155, compound

HRID 1532142Notes

Reaction equation

HRID 1532142 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=1.[O:17]([C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([CH2:31][CH2:32][CH3:33])[CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:31]([C:26]1[CH:25]=[C:24]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:29]=[CH:28][C:27]=1[O:30][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:8][CH:7]=1)[CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 10803177Methyl 2-[4-(3-bromopropoxy)phenyl]acetateHCID 154629044-Phenoxy-2-propylphenol

Product 1

HCID 22459155HCID 22459155, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the product from Step A (11.0 g, 38.58 mmol), 4-phenoxy-2-propylphenol (PCT Application WO97/28115; 8.0 g, 35.07 mmol) and cesium carbonate (12.0 g, 36.82 mmol) in DMF (80 mL) was stirred at 40° C. overnight. The reaction mixture was partitioned between ethyl acetate and 0.2N HCl. The organic layer was washed twice with water, then dried over sodium sulfate. The organic layer was filtered and evaporated to an oil which was chromatographed over silica gel with 10% of ethyl acetate in hexane to afford the title compound.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and 0.2N HCl
  2. washThe organic layer was washed twice with water
  3. dry with materialdried over sodium sulfate
  4. filtrationThe organic layer was filtered
  5. customevaporated to an oil which
  6. customwas chromatographed over silica gel with 10% of ethyl acetate in hexane

Sources & evidence

ORD record
ord-323ecefd2df944229dacf47f9e85a74c
Source dataset
uspto-grants-2001_03
Patent number
US06200998B1

Reaction notes

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