Acetone, oxime → HCID 86675994, compound

HRID 475426Notes

Reaction equation

[CH3:1][C:2](=[N:4][OH:5])[CH3:3].CC(C)([O-])C.[K+].[Br:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH:27]([O:31][CH2:32][CH3:33])[O:28][CH2:29][CH3:30])=[O:20])=[C:15](F)[CH:14]=1>O1CCCC1.O>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH:27]([O:28][CH2:29][CH3:30])[O:31][CH2:32][CH3:33])=[O:20])=[C:17]([O:5][N:4]=[C:2]([CH3:3])[CH3:1])[CH:18]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a mechanically stirred solution of acetone oxime (20.33 g) in tetrahydrofuran (500 mL) under nitrogen was added a solution of 1M potassium tert-butoxide in tetrahydrofuran (325 mL) while cooling in an ice water bath. The thick white suspension was stirred at 20° C. for 20 min then a solution of (4-bromo-2-fluorophenyl)(2-(diethoxymethyl)phenyl)methanone (Compound 2a) (118 g) in tetrahydrofuran (400 mL) was added over 20 min and the resulting pale orange suspension stirred at room temperature for 1 h then refluxed for 2 h. The reaction mixture was diluted with water (680 mL) and extracted into ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate and evaporated to give the title compound (116 g).

Workup

temperaturewhile cooling in an ice water bath
stirringthe resulting pale orange suspension stirred at room temperature for 1 h
temperaturethen refluxed for 2 h
extractionextracted into ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous magnesium sulfate
customevaporated

Sources & evidence

ORD record: ord-4cf7cff27dc649f3b2ae44f62836422e
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637551B2

Reaction notes

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