Sodium hydride → HCID 54216543, compound

HRID 2225648Notes

Reaction equation

HRID 2225648 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.[F:21][C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=1)[O:25][CH2:26][CH2:27]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][CH2:27][CH2:26][O:25][C:24]2[CH:29]=[CH:30][CH:31]=[C:22]([F:21])[CH:23]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 85257MethanesulfonateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 21890057HCID 21890057, compound

Product 1

HCID 54216543HCID 54216543, 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 dimethylforrnamide (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-fluorophenoxy)ethanol (1.17 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The dichloromethane extract was evaporated and the residue was purified by HPLC (dichloromethane-hexane; 4: 1) and the resulting solids were crystallized from diethyl etherhexane to give 0.84 g of 4-[[2-(3-fluorophenoxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 68°-69° C.

Workup

  1. extractionThe dichloromethane extract
  2. customwas evaporated
  3. customthe residue was purified by HPLC (dichloromethane-hexane; 4: 1)
  4. customthe resulting solids were crystallized from diethyl etherhexane

Sources & evidence

ORD record
ord-f89fa004087347679ba2f29dda87b679
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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