Dimethylformamide → 1-(4-Fluorophenyl)-4-methyl-1H-1,2,3-triazole-5-carbaldehyde

HRID 402429Notes

Reaction equation

HRID 402429 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([CH3:13])[N:10]=[N:9]2)=[CH:4][CH:3]=1.[Li]CCCC.CN([CH:22]=[O:23])C.[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH:22]=[O:23])=[C:11]([CH3:13])[N:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 199146881-(4-Fluorophenyl)-4-methyl-1H-1,2,3-triazoleHCID 178418339Butyllithium

Product 1

HCID 199146531-(4-Fluorophenyl)-4-methyl-1H-1,2,3-triazole-5-carbaldehydeYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-75 °C

Procedure

To a solution of 1-(4-fluoro-phenyl)-4-methyl-1H-[1,2,3]triazole (3.67 g, 21 mmol) in THF (110 mL) was added n-BuLi (1.6 M in hexane, 15.53 mL, 25 mmol) dropwise at −75° C. under Argon. The resulting solution was stirred at −75° C. for 1 h, then DMF (2.1 mL, 27 mmol) was added dropwise at −75° C. and the reaction mixture was allowed to warm up to room temperature over 1 h. The mixture was then poured into saturated ammonium chloride solution and 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 (3.85 g, 91%) as a white solid. MS: m/e=206.2 [M]+.

Workup

  1. temperatureto warm up to room temperature over 1 h
  2. extractionextracted 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-448c42c2b76548f59874c62f9a151e35
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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