Diazomethane → HCID 12068821, compound

Participants

Reaction Steps

35 mL (0.349 mol) of 40% aqueous KOH was covered with 100 mL diethyl ether and cooled in the ice bath, and 23.64 g (0.101 mol) of N-methyl-N-nitrosourea was added batchwise, then the mixture was stirred for 10 minutes. Then the ether phase was decanted off, again combined with diethyl ether, swirled around, and decanted off. The combined organic phases were dried over solid KOH while cooling with an ice bath and the solution obtained was further used. 25 mL of the diazomethane solution prepared above and then 53.4 mg (0.000139 mol) of bis(benzonitrile)dichloropalladium(II) was added to a solution of 4.01 g (0.028 mol) of tropenol in 25 mL diethyl ether and 5 mL of methanol while cooling with an ice bath. A further 8 mL of the diazomethane solution was added, then two lots of 10 mL of diazomethane solution, each after 30 minutes, and the mixture was then stirred for another 30 minutes. The solvent was concentrated by evaporation, extracted with hot hexane, filtered hot, evaporated to dryness. Yield: 4.25 g of slightly yellowish crystals (96% of theory).

Provenance & Evidence