N,N-Dimethylbenzamide → HCID 22555997, compound

Participants

Reaction Steps

Combined under Ar 108 (3.00 g, 13.2 mmol) and tetrahydrofuran. Cooled in an IPA/dry ice bath. Added dropwise n-butyllithium solution (2.5M in hexanes, 11.1 mL, 27.8 mmol). Stirred 0.5 h with cooling then warmed over 0.5 h to −15° C. Recooled using IPA/dry ice and added a tetrahydrofuran solution of N,N-dimethylbenzamide (2.38 g, 15.8 mmol). Warmed to room temperature and quenched with water. Removed solvent in vacuo; added sat. sodium bicarbonate and extracted with ethyl acetate (3×). Dried combined organic portions with sodium sulfate (anh.), filtered, removed solvent in vacuo. A solid resulted which was triturated with ether to give 109 as a white solid (3.11 g, 9.39 mmol, 71.2%).

Provenance & Evidence