Potassium Carbonate → HCID 14329995, compound

HRID 2231468Notes

Reaction equation

HRID 2231468 reaction equation
[Cl:1][C:2]1[C:3]([OH:15])=[C:4]([CH2:12][CH2:13][CH3:14])[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.[CH2:16]([O:18][C:19](=[O:45])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[C:24]([O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36]OS(C)(=O)=O)[C:23]=1[CH2:42][CH2:43][CH3:44])[CH3:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C)C=O>[CH2:16]([O:18][C:19](=[O:45])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28](=[O:30])[CH3:29])=[C:24]([O:31][CH2:32][CH2:33][O:34][CH2:35][CH2:36][O:15][C:3]2[C:2]([Cl:1])=[CH:7][C:6]([C:8](=[O:10])[CH3:9])=[C:5]([OH:11])[C:4]=2[CH2:12][CH2:13][CH3:14])[C:23]=1[CH2:42][CH2:43][CH3:44])[CH3:17]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 133891721-(5-Chloro-2,4-dihydroxy-3-propylphenyl)ethan-1-oneHCID 54223276HCID 54223276, compound

Product 1

HCID 14329995HCID 14329995, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.512 g (0.00224 mol) of 1-(5-chloro-2,4-dihydroxy-3-propylphenyl)ethanone, 1.000 g (0.00224 mol) of [4-acetyl-3-[2-[2-[(methylsulfonyl)oxy]ethoxy]ethoxy]-2-propylphenoxy]acetic acid ethyl ester and 0.620 g (0.00448 mol) of anhydrous potassium carbonate in 20 ml of anhydrous acetone and 10 ml of anhydrous dimethylformamide was stirred at reflux for 24 hours. The reaction mixture was filtered and concentrated in vacuo to an oil which was treated with ethyl acetate and sodium chloride solution. The crude oil obtained on concentration of the ethyl acetate was purified by column chromatography, eluting with 20-30% ethyl acetate-hexane to yield 0.400 g (31% yield) of [4-acetyl-3-[2-[2-(4-acetyl-6-chloro-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]2-propylphenoxy]acetic acid ethyl ester as a pale yellow oil.

Workup

  1. temperatureat reflux for 24 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo to an oil which
  4. additionwas treated with ethyl acetate and sodium chloride solution
  5. customThe crude oil obtained on concentration of the ethyl acetate
  6. customwas purified by column chromatography
  7. washeluting with 20-30% ethyl acetate-hexane

Sources & evidence

ORD record
ord-2b3a6ea34220440a9e13f6ba7a207c9d
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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