tert-Butanol → 4-(4-Trifluoromethylbenzyloxy)-2-picoline-N-oxide

HRID 1196621Notes

Reaction equation

HRID 1196621 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]([F:18])([F:17])[C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=1.Cl[C:20]1[CH:21]=[C:22]([CH3:27])[N+:23]([O-:26])=[CH:24][CH:25]=1.C(O)(C)(C)C>O>[F:7][C:8]([F:17])([F:18])[C:9]1[CH:16]=[CH:15][C:12]([CH2:13][O:14][C:20]2[CH:21]=[C:22]([CH3:27])[N+:23]([O-:26])=[CH:24][CH:25]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 676844-(Trifluoromethyl)benzenemethanolHCID 122118014-Chloro-2-methyl-1-oxo-1lambda~5~-pyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 144259584-(4-Trifluoromethylbenzyloxy)-2-picoline-N-oxide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

11.2 g (100 mmol) of potassium tert.-butoxide are added under an N2 atmosphere at 25° C. to 25 ml (183 mmol) of 4-trifluoromethylbenzyl alcohol. 7.2 g (50 mmol) of 4-chloro-2-picoline-N-oxide are subsequently added dropwise, then 10 ml of tert.-butanol are added, and the mixture is stirred for 1 hour at 25° C. and for 30 minutes at 75°-80° C. Water is then added and the mixture is extracted three times using dichloromethane, the extracts are dried and concentrated, and the residue is chromatographed on silica gel using dichloromethane/methanol. The product is obtained from the corresponding fractions, m.p. 113°-115° C.

Workup

  1. extractionthe mixture is extracted three times
  2. customthe extracts are dried
  3. concentrationconcentrated
  4. customthe residue is chromatographed on silica gel
  5. customThe product is obtained from the corresponding fractions, m.p. 113°-115° C.

Sources & evidence

ORD record
ord-d003ff1a25364c99998270b1ea6a741b
Source dataset
uspto-grants-1992_05
Patent number
US05114955

Reaction notes

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