Diisobutylaluminumhydride → (1,3,5-Triethyl-1H-pyrazol-4-yl)-acetaldehyde
Reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[C:7]([CH2:15][CH3:16])=[N:8][N:9]([CH2:13][CH3:14])[C:10]=1[CH2:11][CH3:12])C.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[CH2:13]([N:9]1[C:10]([CH2:11][CH3:12])=[C:6]([CH2:5][CH:4]=[O:3])[C:7]([CH2:15][CH3:16])=[N:8]1)[CH3:14]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Cool a solution of (1,3,5-triethyl-1H-pyrazol-4-yl)-acetic acid ethyl ester (0.92 g, 3.86 mmol) in tetrahydrofuran (50 mL) to −78° C. and add diisobutylaluminum hydride (16.2 mL, 16.2 mmol, 1 M in toluene) dropwise. Stir the resulting mixture for 5 hr. at −78° C. Quench the reaction mixture with saturated aqueous potassium sodium tartrate solution (30 mL) and ethyl acetate (100 mL) and stir at room temperature for 16 hr. Separate the organic layer; dry (sodium sulfate), filter and concentrate to give the title preparation as an oil (0.65 g, 87%). 1H-NMR (400 MHz, CDCl3) δ 9.57 (t, 1H), 4.01 (q, 2H), 3.38 (d, 2H), 2.57 (q, 4H), 1.39 (t, 3H), 1.20 (t, 3H), 1.15 (t, 3H).