Sodium hydride → 4-[[4-(2-Naphthalenyloxy)butyl]oxy]-alpha-oxobenzeneacetic acid methyl ester

HRID 2225688Notes

Reaction equation

HRID 2225688 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+].Br[CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=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][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:31]=[CH:30][C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH:23]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 41306352-(4-bromobutoxy)naphthalene

Product 1

HCID 537942984-[[4-(2-Naphthalenyloxy)butyl]oxy]-alpha-oxobenzeneacetic acid methyl esterYield 72.5%

Reagents, catalysts & solvents 1

HCID 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-(4-bromobutoxy)naphthlene (1.12 g). The mixture was stirred and heated under argon at 60° C. overnight and worked up as in Example 20. The material from dichloromethane extraction was crystallized from dichloromethane-diethyl ether to provide 1.1 g of 4-[[4-(2-naphthalenyloxy)butyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 93°-95° C.

Workup

  1. stirringThe mixture was stirred
  2. extractionThe material from dichloromethane extraction
  3. customwas crystallized from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-0edc02ee762a4f1fb03948b4cc8124e2
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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