2,2,2-Trifluoroethanol → Pyridine, 3-methoxy-2-methyl-4-(2,2,2-trifluoroethoxy)-, 1-oxide

HRID 2258302

Reaction equation

CC(C)([O-])C.[K+].[CH2:7]([OH:12])[C:8]([F:11])([F:10])[F:9].[CH3:13][C:14]1[C:19]([O:20][CH3:21])=[C:18](Cl)[CH:17]=[CH:16][N+:15]=1[O-:23]>O>[CH3:13][C:14]1[C:19]([O:20][CH3:21])=[C:18]([O:12][CH2:7][C:8]([F:11])([F:10])[F:9])[CH:17]=[CH:16][N+:15]=1[O-:23]

Participants

Conditions

Temperature: 0 °C

Procedure

6.7 g of potassium tert-butoxide were added in portions, at -20° C., while stirring and under a nitrogen atmosphere, 5 to 20 ml of trifluoroethanol. After the mixture had been warmed to 0° C., 5.2 g (30 mmol) of 2-methyl-3-methoxy-4-chloropyridine N-oxide were added in portions. The mixture was heated under reflux for 3 hours, and then left to cool down to room temperature; a further 3.45 g of potassium tert-butoxide were then added and the mixture was heated under reflux for 2 hours. After it had cooled down, 40 ml of water were added to the reaction mixture, which was then extracted with dichloromethane; the extract was then dried over MgSO4 and freed from the solvent in vacuo. The resulting oily product was subjected to further reaction.

Workup

temperatureThe mixture was heated
temperatureunder reflux for 3 hours
waitleft
temperatureto cool down to room temperature
temperaturethe mixture was heated
temperatureunder reflux for 2 hours
temperatureAfter it had cooled down
extractionwas then extracted with dichloromethane
dry with materialthe extract was then dried over MgSO4
customThe resulting oily product was subjected to further reaction

Sources & evidence

ORD record: ord-6da0327bc5974c779ac08df838b8c9f5
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05658933

Linked notes

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