Diisobutylaluminum hydride → HCID 59278372, compound

Participants

Reaction Steps

To a chilled (−78° C.) solution of 2-bromo-6-methyl-isonicotinic acid methyl ester (1.90 g, 8.26 mmol) in CH2Cl2 (200 mL) was added a 1 M solution of DIBAH (24.8 mL, 24.8 mmol) in CH2Cl2. The mixture was allowed to warm to room temperature. After 12 hours, the reaction was quenched with saturated aqueous sodium bicarbonate (100 mL). After 5 hours, phases were separated and the aqueous layer was extracted with CH2Cl2 (3×100 mL). The combined organic layers were washed with brine (100 mL), dried over MgSO4, filtered and concentrated. The resulting residue was purified by silica gel chromatography eluting with a gradient of 0-100% ethyl acetate in heptane to afford (2-bromo-6-methyl-pyridin-4-yl)-methanol as white solid. MS m/z 202.45 (M+), 204.44 (M+2).

Provenance & Evidence