Ammonia → (+)-7,8-dihydro-6,6-dimethyl-7-hydroxy-8-amino-6H-pyrano[2,3-f]benz-2,1,3-oxadiazole

Participants

Reaction Steps

0.82 g of 7,8-dihydro-6,6-dimethyl-7,8-epoxy-6H-pyrano [2,3-f] benzo-2,1,3-oxadiazole (3.8 m mols) dissolved in 25 ml of 16.7% NH3 --EtOH solution was reacted in a pressure glass tube at 60° C. for 48 hours. The reaction solution was distilled off and the residue was subjected to a silica gel column chromatography using a developing solvent of ethyl acetate-methanol (5:1 (v/v)) to obtain 0.77 g (yield: 87%) of the intended compound as a brown solid. A part of the obtained compound was recrystallized from ethanol to obtain pure intended compound as colorless crystals.

Provenance & Evidence