Sodium hydride → HCID 54279774, compound

HRID 2225644Notes

Reaction equation

HRID 2225644 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]([CH2:28][CH2:29]O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O.ClCCl>[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:29][CH2:28][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 31236PhenoxyethanolHCID 85257MethanesulfonateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester

Product 1

HCID 54279774HCID 54279774, compoundYield 61.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (1.81 g) in dimethylformamide (25 mL) under argon was treated with 55% sodium hydride (0.437 g), stirred for 15 minutes and treated with the mesylate of 2-phenoxyethanol (2.38 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The crude residue in dichloromethane was passed through a plug of silica gel (5 g) and evaporated and the resulting solids were crystallized from diethyl ether-hexane to give 1.85 g of alpha-oxo-4-[[2-(phenoxy)ethyl]oxy]benzeneacetic acid methyl ester mp 79°-81° C.

Workup

  1. customevaporated
  2. customthe resulting solids were crystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-430daebac6d949d8a4c07b281d2aa05a
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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