Diisobutylaluminum hydride → HCID 69722817, compound

Participants

Reaction Steps

To a cooled solution (-70° C.) of 2-phenyl-8-oxopyrano[4,3-b]pyridine (1.09 g, 4.84 mmol) in dichloromethane (25 ml) was added DIBAL (1M in dichloromethane, 9 ml) keeping the temperature below -65° C. The reaction mixture was held at -70° C. for 4 hours. The reaction mixture was quenched by adding MeOH/dichloromethane (5 ml) (1/1), allowed to warm to ambient temperature and poured onto a slurry of SiO2 and dichloromethane. The silica slurry was applied to the top of a chromatography column which was eluted with methanol/dichloromethane to give 2-phenyl-8-hydroxypyrano[4,3-b]pyridine as a pale yellow solid (0.89 g, 81%). (It was used immediately in the following step)

Provenance & Evidence