2-Ethylbutyraldehyde → HCID 68593369, compound

HRID 748062Notes

Reaction equation

HRID 748062 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

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 2h 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. customquenched with saturated aqueous ammonium chloride
  2. extractionextracted with EtOAc
  3. dry with materialdried over Na2SO4
  4. customAfter removal of the solvents
  5. customthe product was purified by recrystallization from EtOAc/hexanes

Sources & evidence

ORD record
ord-d038e21655c34f80bd9df7aae641219a
Source dataset
uspto-grants-2008_07
Patent number
US07399778B2

Reaction notes

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