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

HRID 2365220Notes

Reaction equation

HRID 2365220 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-b702bcbb16f3474292e24c6b7dd6f21b
Source dataset
uspto-grants-2014_04
Patent number
US08697696B2

Reaction notes

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