Sodium Hydroxide → 4,7-Dihydro-2H-4,7-ethanoisoindole

Participants

Reaction Conditions

Reaction Steps

Fed into a light-shielded reaction vessel equipped with a reflux condenser were 1.95 g (9.6 mmol) of ethyl-4,7-dihydro-4,7-ethano-2H-isoindole-1-carboxylate synthesized in Step 1-2, 100 ml of ethylene glycol, and 2.0 g of sodium hydroxide. Then, the vessel was replaced with nitrogen and the mixture was stirred at 175° C. for 2 hours. After that, the reaction solution cooled to room temperature was poured into ice water, the whole was extracted with chloroform, and the extract was washed with a saturated salt solution. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to yield 4,7-dihydro-4,7-ethano-2H-isoindole (0.98 g, 70.4% yield).

Provenance & Evidence