Sodium hydride → 4-[[3-(2-Naphthalenyl)propyl]oxy]-alpha-oxobenzeneacetic acid methyl ester

HRID 2225694Notes

Reaction equation

HRID 2225694 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][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=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][C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 118175292-(3-Bromopropyl)naphthalene

Product 1

HCID 540032964-[[3-(2-Naphthalenyl)propyl]oxy]-alpha-oxobenzeneacetic acid methyl esterYield 20.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (1.01 g) in dimethylformamide (10 mL) under argon was treated with 55% sodium hydride (0.262 g), stirred for 15 minutes and treated with 2-(3-bromopropyl)naphthalene (1.7 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The material from dichloromethane extraction was purified by HPLC (dichloromethane-hexane; 4:1) and crystallized from diethyl ether-hexane to provide 0.4 g of 4-[[3-(2-naphthalenyl) propyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 97°-99° C.

Workup

  1. extractionThe material from dichloromethane extraction
  2. customwas purified by HPLC (dichloromethane-hexane; 4:1)
  3. customcrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-1d670dee82d34791a1b1a8751e413fca
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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