Dibutyltin oxide → HCID 178438909, compound

Participants

Reaction Conditions

Reaction Steps

Dibutyl tin oxide (15.1 mg, 10% mol) and 2 equivalents of trimethylsilyl azide (0.19 ml, 1.46 mmol), are added successively to a solution of the (E) compound 4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-propenyl]benzonitrile (0.24 g, 0.73 mmol) in anhydrous toluene (1.25 ml). The reaction medium is heated for 16 hours at reflux (110° C.) under an atmosphere of argon and with magnetic stirring. The mixture is purified by flash chromatography on silica (eluent CH2Cl2 then MeOH:CH2Cl2=5:95) to obtain, after evaporation, 0.13 g of a white powder (E) 5-[4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-propenyl]phenyl]-1H-tetrazole (compound CB62458) (yield=48%).

Provenance & Evidence