Nitroethane → HCID 14090006, compound

Participants

Reaction Conditions

Reaction Steps

Under an inert atmosphere a solution of nitroethane (5.36 g, 5.1 ml, 71.4 mmol) in ether (20 ml) was treated at room temperature with a solution of cyclohex-2-enone (6.73 g, 6.78 ml, 70 mmol) in ether (120 ml) followed by the addition of triethylamine (70.8 mg, 97.6 μl, 700 μmol) and the dropwise addition (appr. 1 minute) of phenyl isocyanate (17.0 g, 15.6 ml, 143 mmol). The clear solution was stirred at 25° C. for 48 hours while solid started to precipitate after 2 hours. For the workup, the solid material was filtered and washed three times with ether. The yellow filtrate was evaporated, then the yellow crude product was suspended in dichloromethane (30 ml), the solid was filtered off and washed three times with dichloromethane. After evaporation of the filtrate the crude product was purified by flash chromatography on silica gel using a gradient of heptane and ethyl acetate=5:1 to 4:1 to 1:1 as the eluent. The rac-(3aR,7aR)-3-methyl-5,6,7,7a-tetrahydrobenzo[d]isoxazol-4(3aH)-one (7.27 g, 68% yield) was obtained as an orange liquid. MS: m/z=154.1 [M+H]+. In addition, the rac-(3aR,7aS)-3-methyl-3a,5,6,7a-tetrahydro-4H-benzo[d]isoxazol-7-one (0.52 g, 4.9% yield) was obtained as a light brown solid. MS: m/z=154.1 [M+H]+.

Provenance & Evidence