Hydrochloric Acid → HCID 22101533, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of ethanol (40 ml) containing the 4-(N-acetylbenzylamino)-5-methoxy-2,6,6-trimethyl-2-cyclohepten-1-one methyloxime obtained in step 3 (8.5 g, 23.7 millimoles) there were added pyruvic acid (4.18 g, 47.4 millimoles) and 6N hydrochloric acid (40 ml), and the mixture was heated at 75° C. for 4 hours. The reaction solution was concentrated and the resulting residue was dissolved in methanol (50 ml) and then neutralized with a 10% aqueous sodium hydroxide solution while stirring on ice. Water (100 ml) was added, extraction was performed with benzene, and after washing the benzene solution with water it was dried over anhydrous magnesium sulfate. The benzene was distilled off and the resulting residue was subjected to silica gel column chromatography with benzene-ethyl acetate (19:1) as the eluent, to obtain 4.72 g (69%) of 4-benzylamino-5-methoxy-2,6,6-trimethyl-2-cyclohepten-1-one as a colorless oil.

Provenance & Evidence