Sodium hydride → 4-[[3-(4-Fluorophenyl)propyl]oxy]-alpha-oxobenzeneacetic acid methyl ester

HRID 2225634Notes

Reaction equation

HRID 2225634 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+].[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25]Br)=[CH:19][CH:18]=1>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][CH2:25][CH2:24][CH2:23][C:20]2[CH:21]=[CH:22][C:17]([F:16])=[CH:18][CH:19]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 147371331-(3-Bromopropyl)-4-fluorobenzene

Product 1

HCID 541988504-[[3-(4-Fluorophenyl)propyl]oxy]-alpha-oxobenzeneacetic acid methyl esterYield 36.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (1.63 g) in dimethylformamide (20 mL) under argon was treated with 55% sodium hydride (0.394 g), stirred for 15 minutes and treated with 4-fluorophenylpropyl bromide (1.25 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The material was purified on HPLC (dichloromethane-hexane; 4:1) and crystallized from diethyl etherhexane to provide 0.67 g of 4-[[3-(4-fluorophenyl)propyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 42°-43° C.

Workup

  1. customThe material was purified on HPLC (dichloromethane-hexane; 4:1)
  2. customcrystallized from diethyl etherhexane

Sources & evidence

ORD record
ord-53fb738e98ef4f3985930072631bae18
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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