Sodium hydride → HCID 67757651, compound

HRID 2225640Notes

Reaction equation

HRID 2225640 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+].Cl[CH2:17]/[CH:18]=[CH:19]\[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][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]/[CH:18]=[CH:19]\[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3084696Benzeneacetic acid, 4-hydroxy-alpha-oxo-, methyl esterHCID 10997235[(1Z)-3-Chloro-1-propen-1-yl]benzene

Product 1

HCID 67757651HCID 67757651, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A stirred mixture of 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester (1.79 g) in dimethylformamide (30 mL) under argon was treated with 55% sodium hydride (0.432 g), stirred for 15 minutes and treated with (Z)-(3-chloro-1-propenyl)benzene (1.9 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The crude dichloromethane extract was purified by HPLC (dichloromethane-hexane; 4:1 ) and the resulting 1.9 g of analytically pure (Z)-alpha-oxo-4-[(3-phenyl-2-propenyl)oxy]benzeneacetic acid methyl ester failed to crystallize.

Workup

  1. extractionThe crude dichloromethane extract
  2. customwas purified by HPLC (dichloromethane-hexane; 4:1 )
  3. customto crystallize

Sources & evidence

ORD record
ord-9b783ced4d6f4d3aa2c0b80ed2dfbdbc
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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