Diisobutylaluminumhydride → 5-(2-Hydroxypropan-2-yl)nicotinaldehyde

Participants

Reaction Steps

To a cooled (−78° C.) solution of the title compound from Step B (0.50 g, 2.6 mmol) in toluene (15 mL) and dichloromethane (15 mL) was added a solution of diisobutyl aluminum hydride in toluene (1.0 M, 6.0 mL, 6.0 mmol). After 10 min, the reaction was quenched with water (5 mL), allowed to warm to room temperature and dried with magnesium sulfate. Concentration of the filtrate under reduced pressure provided the title compound: 1H NMR (500 MHz, CDCl3) δ 10.10 (s, 1 H), 8.99 (d, J=2.3 Hz, 1 H), 8.93 (s, 1 H), 8.30 (s, 1 H), 2.22 (br s, 1 H), 1.67 (s, 6 H).

Provenance & Evidence