Sodium hydride → HCID 53855057, compound

HRID 2225710Notes

Reaction equation

HRID 2225710 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+].CS(O[CH2:21][CH2:22][O:23][C:24]1[C:25]2[C:30]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:36]=3[CH:37]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2)(=O)=O>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][CH2:21][CH2:22][O:23][C:24]2[C:25]3[C:30]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:36]=4[CH:37]=2)=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 19004493HCID 19004493, compound

Product 1

HCID 53855057HCID 53855057, compoundYield 50.2%

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 2-(9-phenanthrenyloxy)ethyl methanesulfonate (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 0.8 g of alpha-oxo-4-[[2-(9-phenanthrenyloxy)ethyl]oxy]benzeneacetic acid methyl ester as a yellow solid, mp 147°-148° 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-c524f2e2ea684c72b88c24f4c35efc73
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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