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

HRID 1913650Notes

Reaction equation

HRID 1913650 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-4f162c2699a74bfaa418c30bb4e5cc4d
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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