Formaldehyde → HCID 56928659, compound

Participants

Reaction Steps

A 150-mL single-neck round-bottomed flask equipped with a magnetic stirrer was purged with nitrogen, charged with 117(72 mg, 0.130 mmol), 37% solution of formaldehyde in water (5 mg, 0.170 mmol) and anhydrous methanol (5 mL). A suspension of sodium cyanoborohydride (25 mg, 0.400 mmol) and anhydrous zinc chloride (27 mg, 0.200 mmol) in anhydrous methanol (2.5 mL) was added, and the reaction was stirred at room temperature for 5 h. After this time, the reaction mixture was concentrated, and 10% aqueous potassium carbonate (5 mL) was added. The resulting suspension was filtered, and the filter cake was washed with water (2 mL). The filter cake was purified by column chromatography to afford a 64% yield (56 mg) of 118 as a white solid: mp 201-202° C.; 1H NMR (500 MHz, DMSO-d6) δ 8.66 (s, 1H), 8.54 (s, 1H), 8.11 (s, 1H), 7.72 (d, 2H, J=8.5 Hz), 7.64 (m, 2H), 7.49 (t, 1H, J=8.0 Hz), 7.44 (d, 1H, J=6.5 Hz), 7.37 (m, 2H), 7.27 (d, 1H, J=8.5 Hz), 4.94 (s, 2H), 4.88 (t, 1H, J=4.5 Hz), 4.34 (d, 2H, J=4.5 Hz), 3.59 (s, 3H), 3.54 (t, 2H, J=7.0 Hz), 3.45 (m, 1H), 3.01 (t, 2H, J=6.5 Hz), 2.24 (s, 3H), 1.36 (s, 9H); MS (ESI+) m/z 564.3 (M+H).

Provenance & Evidence