Sodium hydride → HCID 54396318, compound

Participants

Reaction Conditions

Reaction Steps

To a cold (0° C.) suspension of NaH (5.4 g, 60% suspension in mineral oil) in anhydrous ether (180 ml) was added dropwise a mixture of 1-n-butyltosylmethylisocyanide (29 g) and methyl butadienecarboxylate (;2.2 ml) in anhydrous ether (180 ml) and dry dimethyl sulfoxide (90 ml) under an inert atmosphere. The reaction mixture was first stirred at 0° C. for 1 hour and then slowly brought to room temperature and the stirring continued for an additional 6 hours. The reaction mixture was then cooled to 0° C. and cautiously poured onto aqueous saturated ammonium chloride solution (200 ml). The organic layer was separated, and the aqueous layer was thoroughly extracted with ethyl acetate. The combined ether and ethyl acetate extracts were sequentially washed with saturated ammonium chloride solution in cold water, and then brine, and dried with magnesium sulfate. The solvent was removed under vacuum and the residue purified by column chromatography on silica gel, eluting with 15% ethyl acetate/hexane, to afford methyl 3-[ 2-(n-butyl)pyrrol-4-yl]acrylate as a yellow oil (15.32 g), a compound of Formula (AE), which crystallized on standing to a solid, m.p. 65°-67° C.

Provenance & Evidence