Dimethylformamide → HCID 22459155, compound

HRID 2185030Notes

Reaction equation

HRID 2185030 reaction equation
FC1(C2C=CC=C([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)=[CH:22][C:21]=3[CH2:33][CH2:34][CH3:35])C=2)SC(=O)NC1=O.O([C:43]1[CH:48]=[CH:47][C:46](O)=[C:45]([CH2:50][CH2:51]C)[CH:44]=1)C1C=CC=CC=1.[C:53](=O)([O-])[O-:54].[Cs+].[Cs+].CN(C=[O:63])C>>[CH2:33]([C:21]1[CH:22]=[C:23]([O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:24]=[CH:25][C:20]=1[O:19][CH2:18][CH2:17][CH2:16][O:15][C:48]1[CH:43]=[CH:44][C:45]([CH2:50][C:51]([O:54][CH3:53])=[O:63])=[CH:46][CH:47]=1)[CH2:34][CH3:35]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 9848632HCID 9848632, compoundHCID 154629044-Phenoxy-2-propylphenol

Product 1

HCID 22459155HCID 22459155, compound

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-bdc8da64ba1745abb1a7d2c80f586e1b
Source dataset
uspto-grants-2002_06
Patent number
US06399640B1

Reaction notes

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