Triacetoxyperiodinane → Methyl 2-formylisonicotinate

Participants

Reaction Steps

Methyl 2-(hydroxymethyl)isonicotinate (8.36 g, 50 mmol) (from reference compound 38, step 1) was dissolved in dichloromethane (150 mL). Dess-Martin periodinane (25 g, 58.94 mmol) was added and the mixture stirred at room temperature for 2 h 30 min. Sodium sulfothioate (59.3 g, 375.00 mmol) was dissolved in satd NaHCO3 and added to the reaction mixture. The suspension was vigorously stirred at room temperature for 15 min, DCM was added and the phases were separated. The aqueous phase was extracted with DCM twice and the combined organic layers were dried over MgSO4 and evaporated. The residue was purified by automated flash chromatography on a Biotage® KP-SIL 340 g column. Gradient heptanes/EtOAc 80:20 to 65:35 over 5 CV was used as mobile phase. Methyl 2-formylisonicotinate (7 g, 85%) was isolated as an off-white solid. 1H NMR (400 MHz, cdcl3) δ 4.00 (s, 3H), 8.09 (dd, 1H), 8.49 (s, 1H), 8.95 (d, 1H), 10.15 (s, 1H). MS m/z 165 (M)+

Provenance & Evidence