Dimethylacetylene → Ethyl diazoacetate

Participants

Reaction Steps

Under a nitrogen atmosphere 2-butyn (9.50 g, 176 mmol) was cooled to 0° C. and Rh2(OAc)4 (195 mg) was added. To the resulting suspension was added slowly over a period of 4.5 hours ethyl diazoacetate (8.02 g, 70 mmol). The mixture was stirred for 30 minutes and pentane (30 mL) was added. The solids were removed by filtration over Celite and the filtrate was concentrated in vacuo to afford ethyl 2,3-dimethylcycloprop-2-enecarboxylate (below) as a mixture with ethyl diazoacetate.

Provenance & Evidence