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

HRID 465149

Reaction equation

HRID 465149 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([C:19](=[O:21])[CH3:20])[C:12]([OH:18])=[CH:13][CH:14]=2)[CH:9]=1.Br[C:24]([Br:27])([CH3:26])C.[C:28](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[CH:16][C:15]2[C:10](=[C:11]([C:19](=[O:21])[CH3:20])[C:12]([O:18][CH2:28][CH2:26][CH2:24][Br:27])=[CH:13][CH:14]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 116582,2-DibromopropaneHCID 544071994-[(8-Acetyl-7-hydroxy-2-naphthalenyl)oxy]butanoic acid methyl ester

Product 1

HCID 542496624-[[8-Acetyl-7-(3-bromopropoxy)-2-naphthalenyl]oxy]butanoic acid methyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2.7 g of 4[(8-acetyl-7-hydroxy-2-naphthalenyl)oxy]butanoic acid methyl ester, 9.6 ml of dibromopropane and 1.95 g of anhydrous potassium carbonate in 100 ml of anhydrous acetone was stirred at reflux for 17 hours. The mixture was filtered and the filtrate was concentrated in vacuo to an oil which was purified by open column chromatography (eluting with 2.5%-10% of ethylacetate/toluene) to yield 2.98 g (75%) of 4-[[8-Acetyl-7-(3-bromopropoxy)-2-naphthalenyl]oxy]butanoic acid methyl ester as an oil.

Workup

  1. temperatureat reflux for 17 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo to an oil which
  4. customwas purified by open column chromatography (eluting with 2.5%-10% of ethylacetate/toluene)

Sources & evidence

ORD record
ord-e3988faf879e4e79b47b5c944e268e1f
Source dataset
uspto-grants-1985_10
Patent number
US04550190

Linked notes

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