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

HRID 884887Notes

Reaction equation

HRID 884887 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-a2a665bafa184e6db19604136feb478b
Source dataset
uspto-grants-2012_08
Patent number
US08242133B2

Reaction notes

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