Potassium Carbonate → HCID 14330017, compound

HRID 2231490Notes

Reaction equation

HRID 2231490 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][O:33][CH2:34][CH2:35]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][CH2:35][CH2:34][O:33][CH2:32][CH2:31][O:30][CH2:29][CH2:28][O:27][S:23]([CH3:24])(=[O:25])=[O:26])[C:10]=1[CH2:19][CH2:20][CH3:21])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1107763580322-82-3HCID 14330004Ethyl 4-(4-acetyl-3-hydroxy-2-propylphenoxy)butanoate

Product 1

HCID 14330017HCID 14330017, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4.0 g of 4-(4-acetyl-3-hydroxy-2-propylphenoxy)butanoic acid ethyl ester, 19.9 g of triethylene glycol dimesylate and 3.6 g of anhydrous potassium carbonate in 80 ml of anhydrous acetone and 40 ml of anhydrous dimethylformamide was stirred at reflux for 23 hours. The reaction mixture was filtered and the filtrate was concentrated in vacuo to an oil which was purified by high pressure liquid chromatography using 30% ethyl acetate-toluene to give 3.0 g (45% yield) of 4-[4-acetyl-3-[2-[2-[2-[(methylsulfonyl)oxy]ethoxy]ethoxy]ethoxy]-2-propylphenoxy]butanoic acid ethyl ester as an oil.

Workup

  1. temperatureat reflux for 23 hours
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo to an oil which
  4. customwas purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-7999d2b6f4644f01bc16c5706dfa1a6c
Source dataset
uspto-grants-1988_11
Patent number
US04782176

Reaction notes

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