Potassium Carbonate → 2-[(6-Bromohexyl)oxy]-5-[[3-(ethoxycarbonyl)phenyl]carbonyl]benzenepropanoic Acid Ethyl Ester

HRID 327946Notes

Reaction equation

HRID 327946 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:16]=2)=[O:14])[CH:10]=[CH:9][C:8]=1[OH:26])[CH3:2].[Br:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]Br.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:16]=2)=[O:14])[CH:10]=[CH:9][C:8]=1[O:26][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][Br:28])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123681,6-DibromohexaneHCID 147396575-[3-(Ethoxycarbonyl)benzoyl]-2-hydroxybenzenepropanoic acid ethyl ester

Product 1

HCID 541441992-[(6-Bromohexyl)oxy]-5-[[3-(ethoxycarbonyl)phenyl]carbonyl]benzenepropanoic Acid Ethyl EsterYield 76%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 0.393 g (1.06 mmol) of 5-[[3-(ethoxycarbonyl)phenyl]carbonyl]-2-hydroxybenzenepropanoic acid ethyl ester, 2.06 g (8.44 mmol) of 1,6-dibromohexane, 0.882 g (6.39 mmol) of anhydrous granular potassium carbonate and 15 mL of 2-butanone was stirred and refluxed for 18.5 hrs. The resulting slurry was filtered with suction and the solids were washed thoroughly with ethyl acetate. The filtrate and washes were combined and concentrated in vacuo and the residue was purified by flash chromatography on 75 g of silica gel, eluting with 5:1 hexane-ethyl acetate, giving 0.43 g (75.8%) of the title compound as a colorless oil.

Workup

  1. temperaturerefluxed for 18.5 hrs
  2. filtrationThe resulting slurry was filtered with suction
  3. washthe solids were washed thoroughly with ethyl acetate
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by flash chromatography on 75 g of silica gel
  6. washeluting with 5:1 hexane-ethyl acetate

Sources & evidence

ORD record
ord-57288ed72367439ebe151e9da1de65cc
Source dataset
uspto-grants-1993_12
Patent number
US05273999

Reaction notes

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