Tributylstannane → HCID 9842511, compound

Participants

Reaction Conditions

Reaction Steps

3-Cyano-4-(2,2-dichloro-3-oxocyclobutyl)-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole (3.00 g, 6.77 mmol, Example 1) was dissolved in dry toluene (60 ml) in a dry, nitrogen-flushed flask and cooled to 2° C. 2,2'-Azobisisobutyronitrile (134 mg, 0.81 mmol) was added in one portion followed by dropwise addition of tributyltin hydride (4.73 ml, 17.60 mmol) in dry toluene (10 ml). The mixture was allowed to slowly warm to room temperature and was stirred for 18 hr. The toluene was removed in vacuo and the residue dissolved in acetonitrile (50 ml). This solution was washed with hexane (4×50 ml) to remove organotin residues. The combined hexane fractions were extracted with acetonitrile (50 ml). The acetonitrile phases were combined and the solvent removed in vacuo to give a yellow oil. This was purified by silica chromatography (eluting with 10% diethyl ether/hexane) to yield 2.07 g of the title compound as a white solid.

Provenance & Evidence