Sodium hydride → alpha-Oxo-4-[[(4phenoxy)butyl]oxy]benzeneacetic acid methyl ester

HRID 2225673Notes

Reaction equation

HRID 2225673 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1.[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 70986(4-Bromobutoxy)benzeneHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester

Product 1

HCID 54438110alpha-Oxo-4-[[(4phenoxy)butyl]oxy]benzeneacetic acid methyl esterYield 64.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (0.724 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.175 g), stirred for 15 minutes and treated with (4-bromobutoxy)benzene (1.37 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The material from dichloromethane extraction was purified by HPLC (dichloromethane-hexane; 3:1) and crystallized from dichloromethane-hexane to provide 0.85 g of alpha-oxo-4-[[(4phenoxy)butyl]oxy]benzeneacetic acid methyl ester, mp 57°-59°C.

Workup

  1. extractionThe material from dichloromethane extraction
  2. customwas purified by HPLC (dichloromethane-hexane; 3:1)
  3. customcrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-4310132803b2488bbfc24d1834f06ea2
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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