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Water → 4-(4-Fluoro-phenyl)-1-methyl-1H-[1,2,3]triazole

HRID 2365227
Notes
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Reaction equation

HRID 2365227 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[N:10][N:11]([CH2:13][Si](C)(C)C)[CH:12]=2)=[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:9]=[N:10][N:11]([CH3:13])[CH:12]=2)=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962Water2×HCID 2724141Tetrabutylammonium FluorideHCID 674964234-(4-fluoro-phenyl)-1-trimethylsilanylmethyl-1H-[1,2,3]triazole

Product 1

HCID 674955714-(4-Fluoro-phenyl)-1-methyl-1H-[1,2,3]triazoleYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-(4-fluoro-phenyl)-1-trimethylsilanylmethyl-1H-[1,2,3]triazole (5.80 g, 23 mmol) in THF (85 mL) was added water (840 μL, 47 mmol) and then tetrabutylammonium fluoride (1 M in THF, 27.9 mL, 28 mmol) was added dropwise at 0° C. The reaction mixture was stirred at 0° C. for 1 h. 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, 50 to 100% ethyl acetate in heptane) afforded the title compound (4.0 g, 98%) as an off white solid. MS: m/e=178.1 [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, 50 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-5a7f5cfafefd4e39b5643ebd48cc8e76
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08697696B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes