Trimethylsilyl isocyanate → naphtho[1,2-b]furan-3(2H)-one

Participants

Reaction Conditions

Reaction Steps

N-{3-(2,3-Dihydronaphtho[1,2-b]furyl}-N-hydroxyurea. To a solution of N-{3-(2,3-dihydronaphtho[1,2-b]furyl}-N-hydroxyamine (72 mg, 0.36 mmol) in THF (4 mL) was added trimethylsilylisocyanate (98 μL, 0.72 mmol). The resulting solution was heated at 60° C. for 1 h, then allowed to cool and concentrated under reduced pressure. The residue was dissolved in EtOAC and washed successively with H2O and saturated aqueous NaCl. The solvent was removed in vacuo, and the residue was triturated with Et2O. The solid residue was purified by flash chromatography, eluting with 3% MeOH/CH2Cl2 and recrystallized from MeOH/CH2Cl2 to provide the title compound (31 mg, 35%). m.p. 191°-192° C.

Provenance & Evidence