Hexane → HCID 13575680, compound

Participants

Reaction Steps

A solution of the 7C in 200 ml of tetrahydrofuran (THF) was added slowly drop-by-drop to a stirred mixture of 5.7 g of freshly hexane-washed sodium hydride in 100 ml of THF, under nitrogen, at 25°-28° C. After gas ceased to envolve, 42.6 g of methyl iodide was added drop-by-drop over 5 minutes. The mixture was stirred for 18 hours at room temperature, mixed with ice water, and the resulting mixture was extracted with methylene chloride. The extract was washed with cold water, dried (MgSO4) and the solvent was evaporated. The residue was chromatographed over silica gel, using a 1:24 mixture of THF and hexane as eluent. The first fraction that was collected was recrystallized from ether to give 4-chloro-2,3-dihydro-2-(methoxymethyl)-5-methyl-7-nitrobenzofuran (7D), as a tan solid, m.p.: 117°-119° C.

Provenance & Evidence