Sodium hydride → HCID 53704464, compound

HRID 2225657Notes

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(C1C=CC(C)=CC=1)([O-])(=O)=O.[F:27][C:28]([F:40])([F:39])[C:29]1[CH:38]=[CH:37][C:32]([O:33][CH2:34][CH2:35]O)=[CH:31][CH:30]=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][CH2:35][CH2:34][O:33][C:32]2[CH:37]=[CH:38][C:29]([C:28]([F:27])([F:39])[F:40])=[CH:30][CH:31]=2)=[CH:7][CH:6]=1

Participants

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 tosylate of 2-(4-trifluoromethylphenoxy)ethanol (1.8 g). The mixture was heated at 60° C. overnight and worked up as in Example 20. The material was purified by HPLC (dichloromethane-hexane; 4:1 ) and crystallized from diethyl ether-hexane to provide 1 g of alpha-oxo-4-[[2-(4-trifluoromethylphenoxy)ethyl]oxy] benzeneacetic acid methyl ester, mp 96°-98° C.

Workup

customThe material was purified by HPLC (dichloromethane-hexane; 4:1 )
customcrystallized from diethyl ether-hexane

Sources & evidence

ORD record: ord-8181af16d56a4a4eb58eb2f2844fbb74
Source dataset: uspto-grants-1994_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05344843

Reaction notes

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