Pyridine → 1-(6-Bromo-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]-1-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

6-Bromo-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran] (2.53 g, 9.44 mmol) was dissolved in pyridine (8.39 mL, 104 mmol) and acetic anhydride (1.34 mL, 14.2 mmol) was added followed by DMAP (0.0576 g, 0.472 mmol). The reaction was heated to 85° C. for 90 min. After this time the reaction was concentrated in vacuo and the resulting oil was partitioned between EtOAc and 0.5N HCl. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by column chromatography to give 1-(6-bromo-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran]-1-yl)ethanone.

Provenance & Evidence