Sodium hydride → HCID 54406088, compound

HRID 2225731Notes

Reaction equation

HRID 2225731 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.[N:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([O:31][CH2:32][CH2:33]O)=[CH:23][CH:22]=1>CN(C)C=O.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:13])[C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:33][CH2:32][O:31][C:24]2[C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:21]=[CH:22][CH:23]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 85257MethanesulfonateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 1900450524220-96-0

Product 1

HCID 54406088HCID 54406088, compoundYield 56.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (1.267 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.305 g), stirred for 15 minutes and treated with the mesylate prepared from 1.135 g of 2-(4-quinolyloxy)ethanol. The mixture was heated under argon at 60° C. for 3 hours. The cooled mixture was treated with glacial acetic acid (2 drops) and the volatiles were removed under vacuum. The residue was mixed with dichloromethane and dilute cold sodium bicarbonate solution. The dichloromethane extracts were washed with water, dried (Na2SO4), filtered, and evaporated to give crude product. The material was purified by HPLC (ethyl acetate-methanol; 20: 1) and crystallized from dichloromethane-hexane to provide 1.2 g of alpha-oxo-4-[[2-(4-quinolyloxy)ethyl]oxy]benzeneacetic acid methyl ester as a colorless solid, mp 135°-136° C.

Workup

  1. customthe volatiles were removed under vacuum
  2. additionThe residue was mixed with dichloromethane
  3. additiondilute cold sodium bicarbonate solution
  4. washThe dichloromethane extracts were washed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give crude product
  9. customThe material was purified by HPLC (ethyl acetate-methanol; 20: 1)
  10. customcrystallized from dichloromethane-hexane

Sources & evidence

ORD record
ord-af2feac2dcef4e659eb5c5403ca81ad8
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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