benzo[e][1]benzofuran-1-one

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. to cool concentrated under reduced pressure The residue was dissolved in EtOAc washed successively with H2O and saturated aqueous NaCl The solvent was removed in vacuo The residue was triturated with Et2O recrystallized from MeOH/CH2Cl2 /hexanes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-(2-naphthoxy)acetic acid (3.06 g, 15.1 mmol) and oxalyl chloride (7 mL, 80.3 mmol) was heated at reflux for 45 min, then allowed to cool and concentrated under reduced pressure. The residue was dissolved in toluene, and to this was added aluminium chloride (2.40 g, 18.1 mmol). The resulting mixture was stirred at room temperature for 1 h, then poured into ice. The organic phase was separated and washed with saturated aqueous NaCl. Removal of the solvent in vacuo provided the title compound (2.71 g, 97%). was heated at reflux for 45 min to cool concentrated under reduced pressure The residue was dissolved in toluene poured into ice The organic phase was separated washed with saturated aqueous NaCl Removal of the solvent in vacuo

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. to cool concentrated under reduced pressure The residue was dissolved in EtOAc washed successively with H2O and saturated aqueous NaCl The solvent was removed in vacuo The residue was triturated with Et2O recrystallized from MeOH/CH2Cl2 /hexanes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-(2-naphthoxy)acetic acid (3.06 g, 15.1 mmol) and oxalyl chloride (7 mL, 80.3 mmol) was heated at reflux for 45 min, then allowed to cool and concentrated under reduced pressure. The residue was dissolved in toluene, and to this was added aluminium chloride (2.40 g, 18.1 mmol). The resulting mixture was stirred at room temperature for 1 h, then poured into ice. The organic phase was separated and washed with saturated aqueous NaCl. Removal of the solvent in vacuo provided the title compound (2.71 g, 97%). was heated at reflux for 45 min to cool concentrated under reduced pressure The residue was dissolved in toluene poured into ice The organic phase was separated washed with saturated aqueous NaCl Removal of the solvent in vacuo