3a,4,5,7a-Tetrahydro-1H-isoindole-1,3(2H)-dione → Isoindole

Participants

Reaction Conditions

Reaction Steps

To a suspension of LAH (22.80 g, 600 mmol) in THF (600 mL) at 0° C. was added tetrahydrophthalimide (39.45 g, 260.9 mmol) portionwise. After addition, the reaction mixture was stirred at 60° C. for 18 h, then cooled down to 0° C. and quenched carefully with water (25 mL) followed by 15% KOH aqueous solution (25 mL) and another 75 mL of water. The resulting mixture was stirred at rt for 1 h, and filtered through a pad of Celite, then washed with DCM (500 mL). The filtrate was concentrated in vacuo to give isoindole as yellow oil, which was used directly in the next reaction.

Provenance & Evidence