Cesium carbonate → HCID 22458991, compound

HRID 613403Notes

Reaction equation

HRID 613403 reaction equation
[C:1]1([O:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18]Br)=[C:10]([CH2:20][CH2:21][CH3:22])[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:23][C:24]1[CH:25]=[C:26]([CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH:27]=[CH:28][C:29]=1[OH:30].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[CH2:20]([C:10]1[CH:9]=[C:8]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:13]=[CH:12][C:11]=1[O:14][CH2:15][CH2:16][CH2:17][CH2:18][O:30][C:29]1[CH:28]=[CH:27][C:26]([CH2:31][C:32]([O:34][CH3:35])=[O:33])=[CH:25][C:24]=1[Cl:23])[CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 92625Methyl 3-chloro-4-hydroxyphenylacetateHCID 18772270HCID 18772270, compound

Product 1

HCID 22458991HCID 22458991, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(4-bromobutoxy)-3-propylphenyl phenyl ether (5.7 g, 15.75 mmol), methyl 3-chloro-4-hyrdoxyphenylacetate (3.0 g, 15.00 mmol) and cesium carbonate (5.38 g, 16.50 mmol) in DMF (50 mL) was stirred at 40° C. overnight. The reaction mixturewas 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 mixturewas 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-b2eaaa5f315141a19ca7bbd872fe070a
Source dataset
uspto-grants-1999_12
Patent number
US06008237

Reaction notes

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