Sodium hydride → 2',4'-dichloro-2-(3-pyridyl)acetophenone O-[2-(4-fluorophenoxy)ethyl]oxime

HRID 1681308Notes

Reaction equation

[H-].[Na+].[F:3][C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10]Br)=[CH:6][CH:5]=1.[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[C:22](=[N:30][OH:31])[CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1>CN(C)C=O>[F:3][C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10][O:31][N:30]=[C:22]([C:16]2[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:15]=2[Cl:14])[CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

0.55 g of sodium hydride dispersion (50% in oil) and then 2.20 g of 2-(4-fluorophenoxy)ethyl bromide are added with stirring to a solution of 2.81 g of 2',4'-dichloro-2-(3-pyridyl)acetophenone oxime in 20 ml of dimethylformamide. The reaction mixture is heated to 100° C. and stirred at this temperature for 1 hour. It is then cooled to room temperature and poured onto ice. The aqueous mixture is extracted with methylene chloride, and the organic phase is washed twice with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. After chromatography on silica gel using n-hexane/ethyl acetate (7:3) as the eluent, 2',4'-dichloro-2-(3-pyridyl)acetophenone O-[2-(4-fluorophenoxy)ethyl]oxime is obtained as an E/Z isomer mixture in the form of a slightly yellow oil.

Workup

temperatureIt is then cooled to room temperature
additionpoured onto ice
extractionThe aqueous mixture is extracted with methylene chloride
washthe organic phase is washed twice with water
dry with materialdried over anhydrous magnesium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-bec53edc2e6d43508b3515a95325c476
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05171354

Reaction notes

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