Sodium hydride → HCID 54335854, compound

HRID 2225655Notes

Reaction equation

HRID 2225655 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.[CH3:21][C:22]1[CH:31]=[CH:30][C:25]([O:26][CH2:27][CH2:28]O)=[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][CH2:28][CH2:27][O:26][C:25]2[CH:30]=[CH:31][C:22]([CH3:21])=[CH:23][CH:24]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 848042-(4-Methylphenoxy)ethanolHCID 85257MethanesulfonateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester

Product 1

HCID 54335854HCID 54335854, compoundYield 65.7%

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-methylphenoxy)ethanol (1.15 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The material was purified by HPLC (dichloromethane-hexane; 4:1) and crystallized from diethyl ether-hexane to provide 0.83 g of 4-[[2-(4-methylphenoxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 105°-107° C.

Workup

  1. customThe material was purified by HPLC (dichloromethane-hexane; 4:1)
  2. customcrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-4f32ae617c294b06b3108489fe2a8e94
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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