Sodium hydride → HCID 67757392, compound

HRID 2225636Notes

Reaction equation

HRID 2225636 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][C:23]([F:26])=[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][C:23]([F:26])=[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 536642611-(3-Chloro-1-propen-1-yl)-4-fluorobenzene

Product 1

HCID 67757392HCID 67757392, compoundYield 71.3%

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 1-(3-chloro-1-propenyl)-4-fluorobenzene (0.85 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. Crystallization from diethyl ether-hexane provided 0.9 g of (E)-4-[[3-(4-fluorophenyl)-2-propenyl]oxy]-alpha-oxobenzeneacetic acid methyl ester, mp 84°-85° C.

Workup

  1. customCrystallization from diethyl ether-hexane

Sources & evidence

ORD record
ord-291bfba1943c4feba0a5a5357941eacb
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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