Sodium hydride → alpha-Oxo-4-[[2-(4-phenoxy-phenoxy)ethyl]oxy]benzeneacetic acid methyl ester

HRID 2225662Notes

Reaction equation

HRID 2225662 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+].S([O-])(=O)(=O)C.[O:21]([C:28]1[CH:37]=[CH:36][C:31]([O:32][CH2:33][CH2:34]O)=[CH:30][CH:29]=1)[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][CH2:34][CH2:33][O:32][C:31]2[CH:36]=[CH:37][C:28]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:29][CH:30]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 85257MethanesulfonateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 46767252-(4-Phenoxyphenoxy)ethanol

Product 1

HCID 54565301alpha-Oxo-4-[[2-(4-phenoxy-phenoxy)ethyl]oxy]benzeneacetic acid methyl esterYield 69.8%

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 the mesylate of 2-(4-phenoxyphenoxy)ethanol (1.5 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; 4:1) and crystallized from diethyl ether-hexane to provide 1.1 g of alpha-oxo-4-[[2-(4-phenoxy-phenoxy)ethyl]oxy]benzeneacetic acid methyl ester, mp 97°-98° C.

Workup

  1. extractionThe material from dichloromethane extraction
  2. customwas purified by HPLC (dichloromethane-hexane; 4:1)
  3. customcrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-01ba055295ed413f90682812da5e3648
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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