Formaldehyde → Tert-butyl 6-bromo-3,3-bis(hydroxymethyl)-2-oxoindoline-1-carboxylate

Participants

Reaction Steps

To a solution of tert-butyl 6-bromo-2-oxoindoline-1-carboxylate (5.20 g, 16.7 mmol) in THF (100 mL) was added potassium carbonate (6.91 g, 50.0 mmol) followed by paraformaldehyde (12.00 g, 400 mmol). The resulting suspension was stirred at rt for 90 min. The suspension was cooled and poured into saturated aqueous NaHCO3 and extracted with DCM. Organic extracts were purified by column chromatography (eluting with a gradient of 0-10% MeOH in DCM) to give tert-butyl 6-bromo-3,3-bis(hydroxymethyl)-2-oxoindoline-1-carboxylate as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.90 (1H, s), 7.41 (2H, br. s.), 4.97 (2H, t, J=5.18 Hz), 3.63-3.76 (4H, m), 1.57 (s, 9H).

Provenance & Evidence