2,6-Lutidine → HCID 54442206, compound

Participants

Reaction Steps

To a solution of the product from Step A (0.64 g, 1.34 mmol) in anhydrous THF (30 mL) under nitrogen were added methanesulfonic anhydride (0.349 g, 2.00 mmol) and 2,6-lutidine (0.431 g, 4.02 mmol). After 30 min, an additional quantity of methanesulfonic anhydride (0.349 g, 2.00 mmol) and 2,6-lutidine (0.431 g, 4.02 mmol) was added and the reaction continued for 30 min. Evaporation of the solvent provided a residue which was dissolved in anhydrous DMF (50 mL) and DBN (1 mL) was added. This mixture was heated at reflux temperature for 1 h, cooled, poured into a saturated solution of sodium bicarbonate (100 mL) and extracted with ethyl acetate (2×100 mL). The combined extracts were dried over (MgSO4), filtered and evaporated to a residue which was purified by column chromatography (silica, 5% methanol/methylene chloride) to give a viscous oil (0.35 g, 57%).

Provenance & Evidence