Ethanol → 3a,4,4a,7a,8,8a-Hexahydro-3-methyl-4,8-methanofuro-[3,4-f]-1,2-benzisoxazole-5,7-dione

Participants

Reaction Steps

A solution of 4.0 g (24.4 mmol) of cis-5-norbornene-endo-2,3-dicarboxylic anhydride and 5.8 g (48.8 g) of phenyl isocyanate in 20 ml of tetrahydrofuran is treated dropwise with a solution of 1.83 g (1.76 ml, 24.4 mmol) of nitroethane and 6 drops of triethylamine in 10 ml of tetrahydrofuran. The mixture is maintained with stirring for 1 hour. The reaction mixture is filtered and the filtrate evaporated. Trituration with ethyl ether, filtration and drying gives 3.97 g of crude product. Trituration with 100 ml of ethanol (2 times) gives after filtration and drying 2.28 g of the title compound: m.p. 194°-197° C.

Provenance & Evidence