Formaldehyde → HCID 57595175, compound

Participants

Reaction Steps

A 250 mL round bottom flask equipped with a Dean Stark trap was charged with aldehyde 40 (1.44 g, 3.95 mmol), toluene (120 mL), sarcosine (710 mg, 7.97 mmol), and paraformaldehyde (600 mg, 20.0 mmol), and the reaction was heated under reflux for 12 hours, then concentrated under reduced pressure, dissolved in a minimum volume of acetone, and filtered through a 5 g silica cartridge, which was then washed with 80 mL of acetone. The filtrate was then concentrated under reduced pressure, and not purified further. Yield of 41: 1.65 g (98%). 1H NMR (400 MHz, CDCl3) δ 2.63 (bs, 6H), 2.94 (m, 1H), 3.55 (m, 1H), 4.65 (m, 1H), 4.69 (m, 1H), 5.18 (m, 1H), 6.80 (d, J=5.4 Hz, 1H), 6.97 (d, J=7.6 Hz, 1H), 7.13 (t, J=8.4 Hz, 2H), 7.61 (m, 2H), 7.69 (s, 1H), 8.29 (d, J=5.4 Hz, 1H), 9.56 (d, J=7.6 Hz, 1H). MS (ESI+) 410.2 (under MS conditions, the aminal bond is cleaved and instead an M+1 peak is observed for the resulting 7-C(OH)HCH2N(Me)H product).

Provenance & Evidence