Sodium Hydroxide → HCID 12826447, compound

Participants

Reaction Steps

To a flask equipped with stirrer, reflux condenser and gas inlet there is added under nitrogen a mixture of 6.9 g. (0.020 mole) of (+)-3-(m-nitrophenyl)-5,8-dihydro-6,6,8-trimethyl-5,8-ethano-6H-pyrano[4,3-e]-as-triazine-4-oxide, 20 ml. (0.23 mole) of phosphorous trichloride in 300 ml. of 1,2-dichloroethane. The resulting mixture is refluxed for 6.5 hours and then cooled to room temperature, and poured into a beaker containing 500 g. of ice. To this mixture there is added cautiously 60 ml. of 50% aqueous sodium hydroxide while maintaining stirring for 1 hour. The resulting mixture is then transferred to a separatory funnel and permitted to separate. The layers are partitioned and the aqueous phase extracted twice with 300 ml. of methylene chloride and the extracts combined with the organic phase. The resulting solution is washed once with brine, dried over anhydrous magnesium sulfate, and then concentrated to yield a residue which is then recrystallized from absolute ethanol to give (-)-3-(m-nitrophenyl)-5,8-dihydro-6,6,8-trimethyl-5,8-ethano-6H-pyrano[4,3-e]-as-triazine; m.p. 184° to 185° C.; ORD-1.8°.

Provenance & Evidence