Formaldehyde → HCID 54100857, compound

Participants

Reaction Conditions

Reaction Steps

To the product from 167a (328 mg, 0.97 mmol) was added formic acid (88%, 3 mL) and formaldehyde (37%, 6 mL). The mixture was stirred and heated at 70° C. for 6 h. After cooling to room temperature, the mixture was basified with aqueous 10% NaOH. The solution was then extracted with CH2Cl2 (3X), the combined organic layers were dried (MgSO4), concentrated and chromatographed (silica gel; CH2Cl2, 10:0.3 to 10:1) to afford an oil (130 mg, 53%): 1H NMR (CDCl3, 300 MHz) δ 1.70-1.90 (m, 3H), 2.02 (m, 1H), 2.32 (m, 1H), 2.48 (s, 3H), 2.66 (m, 1H), 3.12 (m, 1H), 3.98 (m, 2H), 5.48 (d, 1H, J=10.5 Hz), 5.76 (d, 1H, J=17.5 Hz), 6.98 (dd, 1H, J=11.0, 17.5 Hz), 7.40 (d, 1H, J=3.0 Hz), 8.00 (d, 1H, J=3.0 Hz); MS (CI/NH3) m/z 253 (M+H)+.

Provenance & Evidence