Triethylamine → 1,3-Cyclohexanedione, 2-diazo-5-phenyl-

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Reaction Steps

A solution of 20.0 g (0.106 mol) of 5-phenyl-cyclohexane-1, 3-dione in 75 ml ethanol was cooled to -10° C. and stirred magnetically under nitrogen. To the mixture was added 10.75 g (0.106 mol) of triethylamine. The tosyl azide (20.95 g 0.106 mol) was added all at once, and the mixture stirred for one hour at 0°-5° C. The solvent was removed under vacuum at a temperature less than 40° C. To the residue was added 200 ml ether, and the mixture extracted with a solution containing 3.1 g potassium hydroxide in 200 ml of water. The ethereal solution was dried over anhydrous MgSO4 filtered and the solvent removed to give a yellow solid which was recrystallized from ethanol-hexane to give 8.38 g (32%) of 2-diazo-5-phenyl-cyclohexane-1, 3-dione as yellow crystals, mp 122°-124° C.

Provenance & Evidence