Potassium Carbonate → 4-[[8-Acetyl-7-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-naphthalenyl)oxy]butanoic acid methyl ester

HRID 1981999Notes

Reaction equation

HRID 1981999 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([C:25](=[O:27])[CH3:26])[C:12]([O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23]Br)=[CH:13][CH:14]=2)[CH:9]=1.[OH:29][C:30]1[C:35]([CH2:36][CH2:37][CH3:38])=[C:34]([OH:39])[CH:33]=[CH:32][C:31]=1[C:40](=[O:42])[CH3:41].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C)C=O>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([C:25](=[O:27])[CH3:26])[C:12]([O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:39][C:34]3[CH:33]=[CH:32][C:31]([C:40](=[O:42])[CH3:41])=[C:30]([OH:29])[C:35]=3[CH2:36][CH2:37][CH3:38])=[CH:13][CH:14]=2)[CH:9]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 536606914-[[8-Acetyl-7-[2-(2-bromoethoxy)ethoxy]-2-naphthalenyl]oxy]butanoic acid methyl ester

Product 1

HCID 543662124-[[8-Acetyl-7-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-naphthalenyl)oxy]butanoic acid methyl esterYield 86%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.6 g of 4-[[8-acetyl-7-[2-(2-bromoethoxy)ethoxy]-2-naphthalenyl]oxy]butanoic acid methyl ester, 0.82 g of 1-(2,4-dihydroxy-3-propylphenyl)-ethanone and 0.73 g of anhydrous potassium carbonate in 33 ml of anhydrous acetone and 11 ml of anhydrous dimethylformamide was stirred at reflux for 16 hours. The mixture was filtered and filtrate was concentrated to an oil. The oil was purified by high pressure liquid chromatography using 50% ethyl acetate-hexane to give 1.72 g (86%) of 4-[[8-acetyl-7-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-naphthalenyl)oxy]butanoic acid methyl ester as an oil.

Workup

  1. temperatureat reflux for 16 hours
  2. filtrationThe mixture was filtered
  3. concentrationfiltrate was concentrated to an oil
  4. customThe oil was purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-4a648fe5b36c4ef0a75941c9a79adb90
Source dataset
uspto-grants-1986_06
Patent number
US04594442

Reaction notes

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