Acetone → Methyl 1-cyanocyclobutane-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

10 g (0.1 mol) of methyl cyanoacetate and 10 mL of anhydrous DMF were mixed under stirring for 10 minutes, followed by adding 33.4 g (0.22 mol) of 1,8-diazabicyclo[5,4,0] undec-7-ene (DBU) at 10-20° C. into the mixture, heating the mixture to 50° C. to allow reaction to take place for 15 minutes, moving the mixture to an ice bath (−5˜−10° C.) of a mixture of liquid nitrogen and acetone, and adding 20.4 g (0.10 mol) of 1,3-dibromopropane dissolved in 10 mL of anhydrous DMF into the mixture to form a reaction solution. The reaction solution was subjected to reaction at 25° C. for 15 minutes, and to further reaction at 70° C. for 30 minutes, followed by evaporating, extracting with CH2Cl2 and deionized water, collecting an organic layer from the extraction, evaporating, purifying using silica column chromatography (eluent: acetone/hexane=8/1), and re-evaporating to obtain a product of 8.74 g (0.063 mol, 62.85%) of 4.

Provenance & Evidence