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Sodium hydride → alpha-Oxo-4-[4-(4-pyridinyl)butoxy]benzeneacetic acid methyl ester

HRID 2225725
Notes
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Reaction equation

HRID 2225725 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[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][CH2:30]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][CH2:30][CH2:29][CH2:28][CH2:27][C:24]2[CH:25]=[CH:26][N:21]=[CH:22][CH:23]=2)=[CH:7][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 85257MethanesulfonateHCID 27846554-PyridinebutanolHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl ester

Product 1

HCID 54486867alpha-Oxo-4-[4-(4-pyridinyl)butoxy]benzeneacetic acid methyl esterYield 30.9%

Reagents, catalysts & solvents 2

HCID 176
Acetic Acid
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (1.086 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.261 g), stirred for 15 minutes and treated with the mesylate prepared from 0.906 g of 4-pyridinebutanol. The mixture was heated under argon at 60° C. for 4 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 dried (Na2SO4), filtered, and evaporated to give crude product. The material was purified by HPLC (hexane-acetone; 2: 1) to provide 0.58 g of alpha-oxo-4-[4-(4-pyridinyl)butoxy]benzeneacetic acid methyl ester as a colorless oil whose NMR was compatible with the desired product.

Workup

  1. customthe volatiles were removed under vacuum
  2. additionThe residue was mixed with dichloromethane
  3. additiondilute cold sodium bicarbonate solution
  4. dry with materialThe dichloromethane extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto give crude product
  8. customThe material was purified by HPLC (hexane-acetone; 2: 1)

Sources & evidence

ORD record
ord-63c69b63f3084e8888618e258be1d907
Source dataset
uspto-grants-1994_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05344843

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes