Dimethylformamide → HCID 12069553, compound

Participants

Reaction Steps

3-Pyridinol (1 eq.) was taken up in a 2:1 (v/v) mixture of DMF:THF (0.9 M). To this was then added, at −15° C., potassium tert-butoxide (1.1 eq.) and the resulting suspension was stirred at −15° C. for 25 min before chloromethyl methyl ether (1.1 eq.) was added dropwise over 15 min. The mixture was then warmed to RT over 1 h and allowed to stir at RT for another 2 h. The reaction mixture was then concentrated in vacuo and the resulting residue partitioned between EtOAc and water. The aqueous layer was separated and back-extracted with EtOAc. The combined organic extracts were then washed with water and brine, dried over Na2SO4, filtered through a short plug of SiO2 and the filtrate concentrated in vacuo to afford the title compound as a colorless oil.

Provenance & Evidence