Ethyl diazoacetate → HCID 21502421, compound

Participants

Reaction Steps

A mixture of 0.01 M of the tetrahydropyranyl ether of 3-cyclopentenol (VII) and 1 g. of copper powder is stirred vigorously and maintained at 100° C. while 0.07 M (8 g.) of ethyl diazoacetate is added over a period of 8 hours. The reaction mixture is then extracted with hexane and chromatographed over aluminum oxide (activity I). Elution first with hexane, and then benzene, and evaporation of the eluates gives ethyl 3-[(tetrahydropyran-2-yl)oxy]bicyclo[3.1.0]hexane-6-carboxylate (VIII) in 55% yield as a liquid, b.p. 133° at 1.1 mm.; λ max. 195 mmμ (pentane); γ 3100, 3075, 3047, 1725, 1272, 1140 and 1020 cm-1.; δ 3.92 (quartet), 1.07 (triplet) p.p.m.

Provenance & Evidence