Diisobutylaluminumhydride → HCID 68595861, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve (3,5-diethyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-acetic acid ethyl ester (0.54 g, 1.88 mmol) in tetrahydrofuran (20 mL) and cool to −78° C. Add diisobutyl-aluminum hydride (7.52 mL, 7.52 mmol, 1 M in toluene) dropwise and continue to stir for 2.5 hr. Warm to room temperature over 1 hr. then quench with saturated aqueous potassium sodium tartrate solution (50 mL). Add ethyl acetate (100 mL) and stir at room temperature for 16 hr. Separate the organic layer, dry (sodium sulfate), filter and concentrate. Purify using silica gel chromatography, eluting with 80:20 hexanes:ethyl acetate, to give 2-(3,5-diethyl-1-pyridin-2-yl-1H-pyrazol-4-yl)-ethanol as a white solid (0.30 g, 66%). 1H-NMR (400 MHz, CDCl3) δ 8.39 (m, 1H), 7.80 (d, 1H), 7.73 (m, 1H), 7.12 (m, 1H), 3.72 (m, 2H), 3.08 (q, 2H), 2.67 (m, 4H), 1.58 (bs, 1H), 1.28 (t, 3H), 1.15 (t, 3H).

Provenance & Evidence