Dibutyltin oxide → HCID 178438909, compound

Participants

Reaction Conditions

Reaction Steps

Dibutyl tin oxide (75 mg, 10% mol) and trimethylsilyl azide (0.97 ml, 7.28 mmol), are added successively to a solution of the (Z) compound 4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-propenyl]benzonitrile (1.20 g, 3.64 mmol) in anhydrous toluene (6.25 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, washing with hexane and drying at the palette pump, 0.99 g of a white powder, the compound (Z) 5-[4-[1-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)-2-propenyl]phenyl]-1H-tetrazole (compound CB92834) (yield=73%).

Provenance & Evidence