2-Ethylbutyraldehyde → HCID 68593443, compound

HRID 2243127Notes

Reaction equation

HRID 2243127 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[CH:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1.C([Li])CCC.[CH2:19]([CH:21]([CH2:24][CH3:25])[CH:22]=[O:23])[CH3:20].CCOC(C)=O>C1COCC1.Cl>[CH2:19]([CH:21]([CH2:24][CH3:25])[CH:22]([C:13]1[N:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[N:10]=[CH:11][CH:12]=1)[OH:23])[CH3:20]

Participants

7

Reactant 4

HCID 73592-EthylbutyraldehydeHCID 8857Ethyl AcetateHCID 122381311-(4-Methoxyphenyl)-1H-pyrazoleHCID 178418339Butyllithium

Product 1

HCID 68593443HCID 68593443, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a chilled reaction vessel at −78° C. containing 1-(4-methoxyphenyl)-1H-pyrazole (Tetrahedron Lett. 39(19), 2941-2944, (1998)) (1.096 g, 6.3 mmol) in THF (40 mL) was added a solution of n-butyllithium (2.5M in hexanes, 2.5 mL, 6.4 mmol) dropwise and the mixture was stirred for 1 h. 2-Ethylbutyraldehyde (0.93 mL, 7.5 mmol) was then added dropwise and, after 15 min, the reaction mixture was warmed to room temperature and stirred for 18 h. The reaction mixture was diluted with 0.1N HCl and stirred for 15 min, then poured into a separatory funnel containing EtOAc. The organic layer was separated, dried over MgSO4, filtered and concentrated in vacuo. The resulting oil was purified by column chromatography (SiO2, EtOAc/hexane, 1:4) to yield a pure oil in 68% yield.

Workup

  1. customTo a chilled reaction vessel at −78° C.
  2. stirringstirred for 18 h
  3. stirringstirred for 15 min
  4. additionpoured into a separatory funnel
  5. customThe organic layer was separated
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting oil was purified by column chromatography (SiO2, EtOAc/hexane, 1:4)
  10. customto yield a pure oil in 68% yield

Sources & evidence

ORD record
ord-33d5001cbf5147f5b4d0f0593d8687c4
Source dataset
uspto-grants-2010_03
Patent number
US07674813B2

Reaction notes

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