Nitroethane → (3aS,6aS)-rel-3-methyl-3a,4,6,6a-tetrahydrofuro[3,4-d]isoxazole

Participants

Reaction Steps

A solution of 2,5-dihydrofuran (5 g, 69.9 mmol) in ether (90 ml) was treated dropwise with a solution of nitroethane (5.46 g, 71.3 mmol) in ether (15 ml) at room temperature. Thereafter, triethylamine (70.7 mg, 699 μmol) was added followed by the dropwise addition of phenyl isocyanate (17.3 g, 143 mmol). The reaction mixture was stirred for 3 days at room temperature. For the workup, the white precipitate was filtered and washed with ether. The filtrate was evaporated and the crude product was purified by chromatography using a gradient of heptane and ethyl acetate=100:0 to 50:50 as the eluent. After a second chromatography the (3aS,6aS)-rel-3-methyl-3a,4,6,6a-tetrahydrofuro[3,4-d]isoxazole (58% yield) was obtained as a yellow oil.

Provenance & Evidence