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

Participants

Reaction Conditions

Reaction Steps

N-{1-(1,2-Dihydronaphtho[2,1-b]furyl}-N-hydroxyurea. To a solution of N-{1-(1,2-dihydronaphtho[2,1-b]furyl}-N-hydroxyamine (698 mg, 3.5 mmol) in THF (10 mL) was added trimethylsilylisocyanate (0.94 mL, 7.0 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. The residue was triturated with Et2O and recrystallized from MeOH/CH2Cl2 /hexanes to provide the title compound (93 mg, 11%). m.p. 194.5°-195.5° C.

Provenance & Evidence