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

HRID 2290437Notes

Reaction equation

HRID 2290437 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([C:23](=[O:25])[CH3:24])[C:12]([O:18][CH2:19][CH2:20][CH2:21]Br)=[CH:13][CH:14]=2)[CH:9]=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][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([C:23](=[O:25])[CH3:24])[C:12]([O:18][CH2:19][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:13][CH:14]=2)[CH:9]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 542496624-[[8-Acetyl-7-(3-bromopropoxy)-2-naphthalenyl]oxy]butanoic acid methyl ester

Product 1

HCID 540026604-[[8-Acetyl-7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-naphthalenyl]oxy]butanoic acid methyl esterYield 63.1%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.8 g of 4-[[8-acetyl-7-(3-bromopropoxy)-2-naphthlenyl]oxy]butanoic acid methyl ester, 1 g of 1-(2,4-dihydroxy-3-propylphenyl)ethanone and 0.9 g of anhydrous potassium carbonate in 30 ml of anhydrous acetone and 6 ml of anhydrous dimethylformamide was stirred at reflux for 15 hours. The mixture was filtered and the filtrate was concentrated in vacuo to an oil which was dissolved in ethylacetate and washed with water, 1N sodium hydroxide solution and sodium chloride solution. The oil resulting from the ethyl acetate extract was purified by flash column chromotography to yield 1.44 g (63%) of 4-[[8-Acetyl-7-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-2-naphthalenyl]oxy]butanoic acid methyl ester as an oil.

Workup

  1. temperatureat reflux for 15 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo to an oil which
  4. dissolutionwas dissolved in ethylacetate
  5. washwashed with water, 1N sodium hydroxide solution and sodium chloride solution
  6. customThe oil resulting from the ethyl acetate
  7. extractionextract
  8. customwas purified by flash column chromotography

Sources & evidence

ORD record
ord-c90f424ccf5a4221883fe2901ec78924
Source dataset
uspto-grants-1986_10
Patent number
US04616091

Reaction notes

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