Potassium Carbonate → 4-[4-Acetyl-3-[2-[2-[(methylsulfonyl)oxy]ethoxy]-ethoxy]-2-propylphenoxy]butanoic acid ethyl ester

HRID 2231467Notes

Reaction equation

HRID 2231467 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([OH:18])[C:10]=1[CH2:19][CH2:20][CH3:21])[CH3:2].[S:23]([O:27][CH2:28][CH2:29][O:30][CH2:31][CH2:32]OS(=O)(=O)C)(=[O:26])(=[O:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C)C=O>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[C:11]([O:18][CH2:32][CH2:31][O:30][CH2:29][CH2:28][O:27][S:23]([CH3:24])(=[O:26])=[O:25])[C:10]=1[CH2:19][CH2:20][CH3:21])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium Carbonate2×HCID 147571Diethylene Glycol DimethanesulfonateHCID 14330004Ethyl 4-(4-acetyl-3-hydroxy-2-propylphenoxy)butanoate

Product 1

HCID 143300094-[4-Acetyl-3-[2-[2-[(methylsulfonyl)oxy]ethoxy]-ethoxy]-2-propylphenoxy]butanoic acid ethyl esterYield 67%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4 g (0.013 mol) of 4-(4-acetyl-3-hydroxy-2-propylphenoxy)butanoic acid ethyl ester, 17 g (0.065 mol) of diethylene glycol dimesylate and 3.6 g (0.026 mol) of anhydrous potassium carbonate in 80 ml of anhydrous acetone and 40 ml of anhydrous dimethylformamide was stirred at reflux for 20 hours. An additional 1.8 g of potassium carbonate was added and reflux was continued for a total of 44 hours. The reaction mixture was filtered and concentrated in vacuo to an orange oil which was treated with ethyl acetate and sodium chloride solution. The yellow oil obtained on concentration of the ethyl acetate was purified by HPLC, eluting with 15% ethyl acetate/toluene to yield 4.1 g (67% yield) of 4-[4-acetyl-3-[2-[2-[(methylsulfonyl)oxy]ethoxy]-ethoxy]-2-propylphenoxy]butanoic acid ethyl ester as a yellow oil.

Workup

  1. temperatureat reflux for 20 hours
  2. temperaturereflux
  3. customwas continued for a total of 44 hours
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated in vacuo to an orange oil which
  6. additionwas treated with ethyl acetate and sodium chloride solution
  7. customThe yellow oil obtained on concentration of the ethyl acetate
  8. customwas purified by HPLC
  9. washeluting with 15% ethyl acetate/toluene

Sources & evidence

ORD record
ord-0323c499dec241fcbe0cc5d56c29bdf8
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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