Sodium hydride → Methyl phenylglyoxalate

HRID 2225683Notes

Reaction equation

HRID 2225683 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8](O)=[CH:7][CH:6]=1.[H-].[Na+].S([O-])(=O)(=O)C.C1(OCCO)C2C(=CC=CC=2)C=CC=1>CN(C)C=O>[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 69734Ethanol, 2-(1-naphthalenyloxy)-HCID 85257MethanesulfonateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester

Product 1

HCID 84835Methyl phenylglyoxalate

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-(1-naphthyloxy)ethanol (1.37 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 etherhexane to provide 0.8 g of 4-[2-(1-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 87°-91° C.

Workup

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

Sources & evidence

ORD record
ord-50d6e4700c814cb997f3f61da0067fd1
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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