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

HRID 2290436Notes

Reaction equation

HRID 2290436 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-ce0450a9450642f8895df6f8d6eac8bc
Source dataset
uspto-grants-1986_10
Patent number
US04616091

Reaction notes

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