Sodium hydride → HCID 53850434, compound

HRID 2225646Notes

Reaction equation

HRID 2225646 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:31]=[CH:30][CH:29]=[CH:28][C:23]=1[O:24][CH2:25][CH2:26]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][CH2:26][CH2:25][O:24][C:23]2[CH:28]=[CH:29][CH:30]=[CH:31][C:22]=2[F:21])=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 85257MethanesulfonateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 218908082-(2-Fluoro-phenoxy)-ethanol

Product 1

HCID 53850434HCID 53850434, compoundYield 62.5%

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-(2-fiuorophenoxy)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 dichloromethane-diethyl ether to give 0.8 g of 4-[[2-(2-fiuorophenoxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 112°-113° 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 dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-c082f6fba0694a2a9fd47b9ee0349a2c
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

Loading…