Diethyl Ether → HCID 123228626, compound

Participants

Reaction Steps

Trimethylsulfoxonium iodide (3.98 g, 18.08 mmol) was added in small portions to a suspension of NaH [0.72 g (60% in mineral oil), 18.08 mmol] in dry DMSO (20 mL). The mixture was stirred until gas evolution ceased and a clear solution was formed (1.5 h). Then, a solution of ethyl(E)-ethyl 3-(4-(allyloxy)phenyl)acrylate (Intermediate E, 4.00 g, 17.22 mmol) in DMSO (10 mL) was trasferred via cannula and the reaction was stirred for additional 1 h. The mixture was poured into brine (150 mL) and extrated with Et2O (100 mL); the organic layer was washed with brine (150 mL), dried over anhydrous Na2SO4 and filtered. Removal of the solvent afforded a yellowish solid, that was purified by column chromatography on silica gel (10% EtOAc/Hexanes), affording 1.96 g of (trans)-ethyl 2-(4-(allyloxy)phenyl)cyclopropanecarboxylate [Rf=0.4 (10% EtOAc/Hexanes), white solid, 46% yield].

Provenance & Evidence