Sodium hydride → HCID 54406942, compound

HRID 2225692Notes

Reaction equation

HRID 2225692 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.[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1[S:31][CH2:32][CH2:33][CH2:34][CH2:35]O>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][CH2:35][CH2:34][CH2:33][CH2:32][S:31][C:22]2[CH:23]=[CH:24][C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:21]=2)=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 85257MethanesulfonateHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 19004316HCID 19004316, compound

Product 1

HCID 54406942HCID 54406942, compoundYield 39.4%

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 the mesylate prepared from 4-(2-naphthylthio)butanol (1.55 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 purified by HPLC (dichloromethane-hexane; 3:1) and crystallized from diethyl etherhexane to provide 0.625 g of 4-[[4-(2-naphthalenylthio)butyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 64°-65° C.

Workup

  1. stirringThe mixture was stirred
  2. extractionThe material from dichloromethane extraction
  3. customwas purified by HPLC (dichloromethane-hexane; 3:1)
  4. customcrystallized from diethyl etherhexane

Sources & evidence

ORD record
ord-a950eaa11d9949bd8d402615bab79114
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

Loading…