4-Fluorophenol → HCID 20131575, compound

HRID 845569Notes

Reaction equation

HRID 845569 reaction equation
[C:1]([C:5]1([C:8]([F:15])([N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)[CH3:9])[CH2:7][O:6]1)([CH3:4])([CH3:3])[CH3:2].[F:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1.[K]>COCCOCCOC>[F:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:7][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([OH:6])[C:8]([F:15])([CH3:9])[N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 5462222PotassiumHCID 20131577HCID 20131577, compound

Product 1

HCID 20131575HCID 20131575, compoundYield 17.8%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

6.0 g of 2-tert.-butyl-2-[1-fluoro-1-(1H-1,2,4-triazol-1-yl)-ethyl]-oxirane, 3.1 g of 4-fluorophenol and 0.4 g of potassium p-fluorophenate in 20 ml of diethylene glycol dimethyl ether are heated at 140° C. for 6 hours. After cooling, the reaction mixture is taken up in ice water and extracted with ethyl acetate. The combined organic phases are washed successively with water, saturated sodium chloride solution, 2N sodium hydroxide solution, water and saturated sodium chloride solution, dried over sodium sulfate and evaporated. Chromatography over silica gel using a 4:1 hexane/ethyl acetate mixture gives 1.6 g of 1-(4-fluorophenoxy)-2-tert.-butyl-2-hydroxy-3-fluoro-3-methyl-3-(1H-1,2,4-triazol-1-yl)-propane as a mixture of diastereomers, melting point 90°-93° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases are washed successively with water, saturated sodium chloride solution, 2N sodium hydroxide solution, water and saturated sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-f2bdd7d26b1f46599c6b6f183a1cfc1b
Source dataset
uspto-grants-1988_07
Patent number
US04758670

Reaction notes

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