Tetrahydrofuran → HCID 86751262, compound

Participants

Reaction Conditions

Reaction Steps

35 ml of a 2.5M solution of butyl lithium were added to 14 ml of TMP in 35 ml THF over a period of 10 minutes at a temperature of -70° C. After stirring at -70° C. for 10 minutes, the reaction mixture was allowed to warm up to 0° C. and kept at 0° C. for 10 minutes. The reaction mixture was then cooled to -70° C. again and a solution of 5.0 g of pyrazine in 25 ml THF was then added over a period of 15-20 minutes, while maintaining the temperature below -60° C. The reaction mixture was then stirred at -70° C. for one hour. 10.4 g of 2-fluoro-6-chlorobenzaldehyde were added, while keeping the temperature below -60° C. and the resulting reaction mixture was then stirred at -70° C. for about two hours. The reaction mixture was allowed to warm slowly to room temperature and stirred overnight. 45 ml of saturated NH4Cl were added to the reaction mixture. Then, 150 ml of methylene chloride were added and the layers were separated. The methylene chloride layer was washed with brine, dried (MgSO4), filtered and stripped to a dark brown residue. The residue was put on a silica gel column and eluted with a 4:1 mixture of hexane:diethyl ether, then 2:1 hexane:diethyl ether. The desired fraction yielded 2.0 g of 2-(1-hydroxy-2'-fluoro-6'-chlorobenzyl)pyrazine in a yellow, semi-solid form.

Provenance & Evidence