Sodium Carbonate → 3,6-Bis-allyloxybenzo[d]isoxazol-5-ylamine

Participants

Reaction Steps

To a solution of 3,6-bis-allyloxy-5-nitrobenzo[d]isoxazole (0.60 g, 2.17 mmol) in EtOAc (12 mL) is added portionwise tin(II) chloride dihydrate (2.2 g, 9.75 mmol). The mixture is stirred at room temperature for 2 h and then at 60° C. for 1.5 h. The mixture is diluted with EtOAc and saturated NaHCO3 is added dropwise, resulting in the formation of a precipitate. Sodium carbonate (2N) is added and the insoluble precipitate is filtered off. The phases are separated and the aqueous phase is extracted with EtOAc (3×). The organic layers are washed with water and brine, dried over MgSO4, filtered and concentrated. The crude material is purified by flash chromatography on silica gel, eluting with a gradient of hexanes/EtOAc to afford 3,6-bis-allyloxybenzo[d]isoxazol-5-ylamine as a waxy solid: (M+H)+=247.2.

Provenance & Evidence