Methyl vinyl ketone → HCID 59397215, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-benzyl-7-(2-fluoroethyl)-7,8-dihydrocyclopenta[e]indazol-6(2H)-one (11.8 g, 38.3 mmol) in dry THF (100 mL) were added 1,8-diazabicyclo[5.4.0]undec-7-ene (12 mL, 80 mmol) and methyl vinyl ketone (6.4 mL, 77 mmol) and the solution was heated to 55° C. After heating for 72 hours, analysis of an aliquot by 1H NMR showed the reaction to be complete. After cooling to room temperature, the solution was partitioned between 5% MeOH/CH2Cl2 and water and the organic phase was washed with 5% aqueous NaHCO3. The solvent was removed by evaporation under vacuum and the residue was purified by chromatography on silica gel (1:2 to 1:1 EtOAc/hexanes) to give 2-benzyl-7-(2-fluoroethyl)-7-(3-oxobutyl)-7,8-dihydrocyclopenta[e]indazol-6(2H)-one as an orange oil.

Provenance & Evidence