4-Methylpyridine → HCID 65582892, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of lithium diisopropylamide (2M solution in THF/heptane/ethylbenzene) (12.00 ml, 24.00 mmol) in tetrahydrofuran (20 ml) at −78° C. under argon was added 4-picoline (1.946 ml, 20 mmol). The reaction mixture was stirred at −78° C. for 15 minutes and a solution of N,2-dimethyl-N-(methyloxy)-3-furancarboxamide (3.38 g, 20.00 mmol) in tetrahydrofuran (5 ml) was added dropwise. The solution was allowed to warm to room temperature over 2 hours. Brine was added and the mixture was extracted with dichloromethane. The organic layer was separated and washed with saturated sodium hydrogen carbonate solution, water and brine, dried and evaporated to give the title compound as a solid (3.72 g, 92%). LC/MS [M+H]+=202.

Provenance & Evidence