Sodium hydride → HCID 53889920, compound

HRID 2225708Notes

Reaction equation

HRID 2225708 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.O[CH2:22][CH2:23][O:24][C:25]1[CH:38]=[CH:37][C:36]2[C:27](=[CH:28][C:29]3[C:34]([CH:35]=2)=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:26]=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][CH2:22][CH2:23][O:24][C:25]2[CH:38]=[CH:37][C:36]3[C:27](=[CH:28][C:29]4[C:34]([CH:35]=3)=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:26]=2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 85257MethanesulfonateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 19004290HCID 19004290, compound

Product 1

HCID 53889920HCID 53889920, compoundYield 46.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 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-hydroxyethoxy)anthracene (1.26 g). The mixture was heated under argon at 60° C. overnight. The cooled mixture was treated with glacial acetic acid (2 drops) and the volatiles were removed under vacuum. The residue was mixed with water and the solids were filtered off, dissolved in dichloromethane, dried (Na2SO4), filtered, and evaporated to give crude product. Crystallization from dichloro-methane-diethyl ether provided 0.75 g of 4-[[2-(2anthracenyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester as a yellow solid, mp 188°-189° C.

Workup

  1. customthe volatiles were removed under vacuum
  2. additionThe residue was mixed with water
  3. filtrationthe solids were filtered off
  4. dissolutiondissolved in dichloromethane
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customto give crude product
  9. customCrystallization from dichloro-methane-diethyl ether

Sources & evidence

ORD record
ord-61e4e9e9bc8e4bd68c4773d8eaf245fd
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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