2,2,3,3,3-Pentafluoropropanol → 2-[3-(2,2,3,3,3-Pentafluoropropoxy)pyridin-4-yl]-5-(trifluoromethyl)benzoxazole

HRID 2190762Notes

Reaction equation

HRID 2190762 reaction equation
F[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[N:12]=1.C(=O)([O-])[O-].[K+].[K+].[F:27][C:28]([F:35])([C:31]([F:34])([F:33])[F:32])[CH2:29][OH:30]>O>[F:27][C:28]([F:35])([C:31]([F:34])([F:33])[F:32])[CH2:29][O:30][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:11]=2[N:12]=1

Participants

5

Reactant 3

HCID 98722,2,3,3,3-PentafluoropropanolHCID 11430Potassium CarbonateHCID 668801802-(3-Fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole

Product 1

HCID 866510552-[3-(2,2,3,3,3-Pentafluoropropoxy)pyridin-4-yl]-5-(trifluoromethyl)benzoxazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.28 g of 2-(3-fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole, 0.27 g of potassium carbonate and 3 ml of 2,2,3,3,3-pentafluoropropanol was heated to reflux while stirring for 5.5 hours. The reaction mixture was cooled to room temperature, and then water was added to the reaction mixture, followed by extraction with ethyl acetate twice. The combined organic layers were washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.33 g of 2-[3-(2,2,3,3,3-pentafluoropropoxy)pyridin-4-yl]-5-(trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 75”).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. extractionfollowed by extraction with ethyl acetate twice
  4. washThe combined organic layers were washed with a saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-074b97d693f243bb8b6127264385333c
Source dataset
uspto-grants-2012_12
Patent number
US08324387B2

Reaction notes

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