2-Ethylbutyraldehyde → HCID 68593369, compound

HRID 2243140Notes

Reaction equation

HRID 2243140 reaction equation
[CH3:1][O:2][C:3]1[CH:14]=[CH:13][C:6]([CH2:7][N:8]2[CH:12]=[N:11][CH:10]=[N:9]2)=[CH:5][CH:4]=1.C([Li])CCC.[CH2:20]([CH:22]([CH2:25][CH3:26])[CH:23]=[O:24])[CH3:21]>C1COCC1>[CH2:20]([CH:22]([CH2:25][CH3:26])[CH:23]([C:12]1[N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:14][CH:13]=2)[N:9]=[CH:10][N:11]=1)[OH:24])[CH3:21]

Participants

5

Reactant 3

HCID 73592-EthylbutyraldehydeHCID 108453281-(4-Methoxybenzyl)-1,2,4-triazoleHCID 178418339Butyllithium

Product 1

HCID 68593369HCID 68593369, compoundYield 114.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1-(4-methoxybenzyl)-1H-1,2,4-triazole (2.12 g, 11.2 mmol) in THF (120 mL) at −78° C. was added a solution of n-butyllithium (2.5 M in hexanes, 4.9 mL, 12.3 mmol) over a period of 20 min. The solution was stirred at −78° C. for 2 h and 45 min. Then 2-ethylbutyraldehyde (0.65 mL, 5.3 mmol) was added. After 1.5 h the reaction mixture was warmed to room temperature, quenched with saturated aqueous ammonium chloride, extracted with EtOAc and dried over Na2SO4. After removal of the solvents, the product was purified by recrystallization from EtOAc/hexanes to give 1.75 g (54%) of 2-ethyl-1-[1-(4-methoxybenzyl)-1H-1,2,4-triazol-5-yl]butan-1-ol as a white solid.

Workup

  1. temperatureAfter 1.5 h the reaction mixture was warmed to room temperature
  2. customquenched with saturated aqueous ammonium chloride
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. customAfter removal of the solvents
  6. customthe product was purified by recrystallization from EtOAc/hexanes

Sources & evidence

ORD record
ord-1213c65304a5421e8a67e027d4f949cd
Source dataset
uspto-grants-2010_03
Patent number
US07674813B2

Reaction notes

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