1,3-Cyclohexanedione → HCID 178515920, compound

Participants

Reaction Steps

To 1,3-cyclohexane dione (22.4 g, 0.19 mol), add tert-butoxybis(dimethylamino)methane (23.1 g, 0.19 mol). Stir the reaction at room temperature for 5 minutes. Add hydrazine dihydrochloride (20.55 g, 0.19 mol) to the reaction and stir at room temperature for 1 hour. Add formic acid (50 mL) to the mixture. Bring the reaction to 100° C. and stirred for 2 hours. Cool the reaction and extract with 3:1 chloroform:IPA (10×60 mL each). Combine the organics and dry over sodium sulfate. After filtration and concentration, load the residue on silica gel column and flash with ethyl acetate to afford 21.6 g (82%) of the desired product as white-grey solid. NMR matches the structure. MS (m/z): 137 [M+H]+.

Provenance & Evidence