Sodium hydride → HCID 54411931, compound

HRID 2225667Notes

Reaction equation

HRID 2225667 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][O:22][C:23]1[CH:24]=[C:25]([CH:30]=[C:31]([O:35][CH3:36])[C:32]=1[O:33][CH3:34])[O:26][CH2:27][CH2:28]O>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:24]=[C:23]([O:22][CH3:21])[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 85257MethanesulfonateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 15101262HCID 15101262, compound

Product 1

HCID 54411931HCID 54411931, compoundYield 63.7%

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-(3,4,5-trimethoxyphenoxy)ethanol (1.8 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The material form dichloromethane extraction was purified by HPLC (dichloromethane-diethyl ether, 50:1) and crystallized from dichloromethane-hexane to provide 1 g of 4-[[2-(3,4,5-trimethoxyphenoxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 82°-83° C. Analysis Calculated for C20H22O8 : C, 61.53; H, 5.68. Found: C, 60.82; H, 5.71.

Workup

  1. customThe material form
  2. extractiondichloromethane extraction
  3. customwas purified by HPLC (dichloromethane-diethyl ether, 50:1)
  4. customcrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-193ed7e272fd4f41b25010c09dd0d05d
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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