Diisopropylethylamine → 3-(2,3-Dihydro-2-methylbenzofuran-7-yl)-5-(N-methoxy-N-methylamino)-1,3,4oxadiazol-2(3H)-one

Participants

Reaction Steps

3.4 g of 1F, 2.5 g of N,N-diisopropyl-N-ethylamine and 75 ml of methanol were mixed. The resulting solution was allowed to stand at room temperature for 18 hours, then was warmed on a steam bath for 24 hours. The solvent was evaporated under reduced pressure and the residue was flash chromatographed over silica gel, a 2:15:33 v:v:v mixture of tetrahydrofuran, ethyl acetate and hexane being used as eluent. One product, Rf =0.14, was obtained as an off-white solid. Recrystallization from ether/hexane gave 2, m.p.: 91°-93° C. A second product, Rf =0.17, was obtained as an off-white solid. Recrystallization from ether/hexane gave 1, m.p.: 147°-149° C.

Provenance & Evidence