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

HRID 1719413Notes

Reaction equation

HRID 1719413 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[C:9]([C:23](=[O:25])[CH3:24])[C:10]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21]Br)=[CH:11][CH:12]=2)[CH:7]=1.[OH:27][C:28]1[C:33]([CH2:34][CH2:35][CH3:36])=[C:32]([OH:37])[CH:31]=[CH:30][C:29]=1[C:38](=[O:40])[CH3:39].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C)C=O>[CH3:1][O:2][C:3](=[O:26])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[C:9]([C:23](=[O:25])[CH3:24])[C:10]([O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:37][C:32]3[CH:31]=[CH:30][C:29]([C:38](=[O:40])[CH3:39])=[C:28]([OH:27])[C:33]=3[CH2:34][CH2:35][CH3:36])=[CH:11][CH:12]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 54307926HCID 54307926, compound

Product 1

HCID 13504776[[8-Acetyl-7-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-naphthalenyl]oxy]acetic acid methyl esterYield 76%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.4 g of [[8-acetyl-7-[2-[2-bromoethoxy)ethoxy]-2-naphthalenyl]oxy]acetic acid methyl ester, 1.32 g of 1-(2,4-dihydroxy-3-propylphenyl)-ethanone and 1.17 g of anhydrous potassium carbonate in 48 ml of anhydrous acetone and 16 ml of anhydrous dimethylformamide was stirred at reflux for 18 hours. The mixture was filtered and filtrate was concentrated to an oil. The oil was purified by flash column chromatography (10% ethyl acetate-toluene) to yield 2.3 g, mp. 89°-90° C. (76%) of [[8-acetyl-7-[2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethoxy]ethoxy]-2-naphthalenyl]oxy]acetic acid methyl ester.

Workup

  1. temperatureat reflux for 18 hours
  2. filtrationThe mixture was filtered
  3. concentrationfiltrate was concentrated to an oil
  4. customThe oil was purified by flash column chromatography (10% ethyl acetate-toluene)

Sources & evidence

ORD record
ord-a307e7adb6b145c5be7e6850b1258eef
Source dataset
uspto-grants-1985_09
Patent number
US04539419

Reaction notes

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