Formaldehyde → HCID 118098727, compound

Participants

Reaction Conditions

Reaction Steps

15D (0.573 g, 1.356 mmol) was dissolved in toluene (5 mL), and to the resulting solution were sequentially added potassium carbonate (0.375 g, 2.71 mmol), paraformaldehyde (0.407 g, 13.56 mmol) and tris(3,6-dioxaheptyl)amine (tda-1) (0.043 mL, 0.136 mmol). The reaction mixture was stirred at 85° C. for 10 h. The reaction mixture was diluted with EtOAc (20 mL) and water (10 mL) and stirred for 15 min. The organic phase was separated, washed with water (3×10 mL), brine (1×10 mL) and dried (Na2SO4). EtOAc was removed under reduced pressure and the residue was purified flash chromatography (0-35% EtOAc/hexanes). Fractions were combined and concentrated under reduced pressure to give 15E (0.187 g, 31.7% yield) as a colorless syrup. MS (ESI) m/z: 435.1 [M+1]+. 1H NMR: (400 MHz, CDCl3) δ ppm 7.40 (1H, d, J=5.77 Hz), 7.06 (2H, d, J=8.28 Hz), 6.50 (1H, s), 5.67 (1H, d, J=1.76 Hz), 4.27-4.39 (2H, m), 4.21 (2H, q, J=7.03 Hz), 2.61-2.77 (3H, m), 1.38-1.55 (18H, m), 1.26 (3H, t, J=7.03 Hz).

Provenance & Evidence