Water → [5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-methanol

HRID 2365213Notes

Reaction equation

HRID 2365213 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[N:11][N:10]([CH2:13][Si](C)(C)C)[C:9]=2[CH2:18][OH:19])=[CH:4][CH:3]=1.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[N:11][N:10]([CH3:13])[C:9]=2[CH2:18][OH:19])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 2724141Tetrabutylammonium FluorideHCID 67496703[5-(4-Fluoro-phenyl)-3-trimethylsilanylmethyl-3H-[1,2,3]triazol-4-yl]-methanol

Product 1

HCID 67498408[5-(4-Fluoro-phenyl)-3-methyl-3H-[1,2,3]triazol-4-yl]-methanolYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of [5-(4-fluoro-phenyl)-3-trimethylsilanylmethyl-3H-[1,2,3]triazol-4-yl]-methanol (616 mg, 2.20 mmol) in THF (37 mL) was added water (79 μL, 4.41 mmol) and then tetrabutylammonium fluoride (1 M in THF, 2.65 mL, 2.65 mmol) added dropwise at 0° C. The reaction mixture was stirred at 0° C. for 15 min. The resulting mixture was poured into water and then the THF was evaporated. The aqueous layer was then extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 100% ethyl acetate in heptane) afforded the title compound (410 mg, 90%) as an off white solid. MS: m/e=208.0 [M+H]+.

Workup

  1. customthe THF was evaporated
  2. extractionThe aqueous layer was then extracted with ethyl acetate
  3. washthe combined organic extracts washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by chromatography (silica, 0 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-6d4fc08c628d4ee9b51a300c33657b41
Source dataset
uspto-grants-2014_04
Patent number
US08697696B2

Reaction notes

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