Potassium Carbonate → Ethyl(4-{4-(benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzyl}-3,5-dimethylphenoxy)acetate

HRID 1836556Notes

Reaction equation

HRID 1836556 reaction equation
[CH2:1]([O:8][C:9]1[CH:24]=[CH:23][C:12]([CH2:13][C:14]2[C:19]([CH3:20])=[CH:18][C:17]([OH:21])=[CH:16][C:15]=2[CH3:22])=[CH:11][C:10]=1[S:25]([C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)(=[O:27])=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:41]([O:44][CH2:45][CH2:46]Br)(=[O:43])[CH3:42].[Cl-].[NH4+]>CN(C)C=O>[CH2:45]([O:44][C:41](=[O:43])[CH2:42][O:21][C:17]1[CH:18]=[C:19]([CH3:20])[C:14]([CH2:13][C:12]2[CH:23]=[CH:24][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:10]([S:25]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)(=[O:26])=[O:27])[CH:11]=2)=[C:15]([CH3:22])[CH:16]=1)[CH3:46]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 25517Ammonium ChlorideHCID 234996174-{4-(Benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzyl}-3,5-dimethylphenol

Product 1

HCID 23499607Ethyl(4-{4-(benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzyl}-3,5-dimethylphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

85 mg (0.18 mmol) of 4-{4-(benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzyl}-3,5-dimethylphenol (Example X) are dissolved in 2 ml of dimethylformamide. 30 mg (0.21 mmol) of potassium carbonate and 33 mg (0.20 mmol) of bromoethyl acetate are added. The mixture is stirred at room temperature overnight. Saturated ammonium chloride solution is then added, and the mixture is extracted three times with diethyl ether. The combined organic phases are washed three times with water, dried with sodium sulphate and concentrated under reduced pressure. This gives 80 mg (96.5% of theory) of ethyl (4-{4-(benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzyl}-3,5-dimethylphenoxy)acetate.

Workup

  1. extractionthe mixture is extracted three times with diethyl ether
  2. washThe combined organic phases are washed three times with water
  3. dry with materialdried with sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e2e4ab9149f448d199757c93ed68153c
Source dataset
uspto-grants-2004_08
Patent number
US06777442B2

Reaction notes

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