Water → 1-Methyl-3-phenyl-1H-1,2,4-triazole-5-carbaldehyde

HRID 2105063Notes

Reaction equation

HRID 2105063 reaction equation
[Li]CCCC.[CH3:6][N:7]1[CH:11]=[N:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:8]1.CN([CH:21]=[O:22])C.O>C1COCC1>[CH3:6][N:7]1[C:11]([CH:21]=[O:22])=[N:10][C:9]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[N:8]1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 108774081-Methyl-3-phenyl-1H-1,2,4-triazoleHCID 178418339Butyllithium

Product 1

HCID 132241431-Methyl-3-phenyl-1H-1,2,4-triazole-5-carbaldehydeYield 86.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

BuLi (10.6 mL, 1.6 M in hexane, 17.0 mmol) was added dropwise to at solution of 1-methyl-3-phenyl-1H-1,2,4-triazole (2.7 g, 17.0 mmol) in THF (85 mL) at −78° C. The mixture was warmed to −40° C. over 15 min and recooled to −78° C. DMF (1.32 mL, 17 mmol) was added dropwise and the mixture was warmed to ambient temperature over 2 h. Water was added to the mixture and it was extracted with EtOAc (3×). The organics were combined, washed with brine, dried (Na2SO4) and concentrated. Purification by flash chromatography (EtOAc, hexanes) yielded 2.75 g of Intermediate 386.1 as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 4.22 (s, 3H) 7.34-7.56 (m, 3H) 8.10 (dd, J=7.58, 1.71 Hz, 2H) 10.03 (s, 1H).

Workup

  1. customrecooled to −78° C
  2. temperaturethe mixture was warmed to ambient temperature over 2 h
  3. extractionwas extracted with EtOAc (3×)
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification by flash chromatography (EtOAc, hexanes)

Sources & evidence

ORD record
ord-72c36757773f410984bb71180f2cb803
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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