Triacetoxyperiodinane → 1-(6-Bromopyridin-3-yl)propan-1-one

Participants

Reaction Steps

To a solution of 1-(6-bromopyridin-3-yl)-propan-1-ol (12.9 g, 59.9 mmol) in THF (200 mL) is added 85% activated Mn02 (6.4 g, 63 mmol) and the mixture is stirred overnight. The reaction is monitored by TLC (EtOAc-hexanes 4:6) indicating starting material and a new less polar product. To the mixture is added additional 85% activated MnO2 (6.0 g, 58.66 mmol) and the mixture stirred for 2 days. The reaction is monitored by TLC (EtOAc-hexanes 3:7) indicating starting material is still present. The mixture is warmed at reflux for 6 hours. The mixture is filtered through filter agent and concentrated. The residue is diluted with dichloromethane and Dess-Martin periodinane (19 g, 44.8 mmol) is added. After 1 hour, the mixture is diluted with saturated aqueous potassium carbonate (200 mL) and concentrated. The resulting solid is collected by filtration washing with water and dried. The solid is suspended in dichloromethane and filtered and the filtrate is passed through a pad of silica gel eluting with ether to afford 1-(6-bromopyridin-3-yl)-propan-1-one as a solid.

Provenance & Evidence