1-Butanol → HCID 178450849, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 2-(1,3-dioxo-5-(o-tolyloxy)isoindolin-2-yl)acetate (10.0 g, 30.8 mmol) in n-butanol (206 mL) at 95° C. was added 1 N sodium n-butoxide solution (62.0 mL, 62.0 mmol). The resulting mixture was stirred at 95° C. for 2 hours before cooling to room temperature. The solvent was partially removed and the residue was diluted with EtOAc (200 mL) and 2 N HCl (40 mL). The resulting mixture was stirred vigorously for 15 minutes at room temperature and the precipitation was collected by filtration. The filter cake was washed with H2O and then dried at 70° C. in vacuo to give a yellow solid. The solid obtained was further suspended in EtOAc (300 mL) and the slurry was heated to reflux with stirring for 2 hours. After cooling to room temperature, the precipitate was collected by filtration and then dried in vacuo to give the title compound in 1.6 g. 1H NMR (CDCl3, 200 MHz): δ=10.38 (s, 1H), 8.42-8.32 (m, 2H), 7.43 (s, 1H), 7.34-7.10 (m, 3H), 7.02 (d, 1H, J=7.6 Hz), 4.39 (t, 2H, J=6.6 Hz)), 2.20 (s, 3H), 1.84-1.38 (m, 4H), 0.99 (t, 3H, J=7.2 Hz).

Provenance & Evidence