Propargyl alcohol → Benzoxazole

HRID 2094401Notes

Reaction equation

HRID 2094401 reaction equation
FC1C=NC=CC=1[C:8]1[O:9][C:10]2[CH:16]=[CH:15][C:14](C(F)(F)F)=[CH:13][C:11]=2[N:12]=1.C(=O)([O-])[O-].[K+].[K+].C(O)C#C>O>[O:9]1[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=[CH:8]1

Participants

5

Reactant 3

HCID 7859Propargyl alcoholHCID 11430Potassium CarbonateHCID 668801802-(3-Fluoropyridin-4-yl)-5-(trifluoromethyl)benzoxazole

Product 1

HCID 9228Benzoxazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

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-propyne-1-ol was stirred while heating at 100° C. for two 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 0.20 g of 2-(3-(2-propyne-1-yloxy)pyridin-4-yl)-5-trifluoromethyl)benzoxazole (hereinafter, referred to as “active compound 73”).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionfollowed by extraction with ethyl acetate twice
  3. washThe combined organic layers were washed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a4e0488c471c42b0a437b5c709fe5689
Source dataset
uspto-grants-2013_05
Patent number
US08445522B2

Reaction notes

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