Formaldehyde → HCID 118098780, compound

Participants

Reaction Conditions

Reaction Steps

36E (0.344 g, 0.916 mmol) was dissolved in toluene (4 mL), and to the resulting solution were sequentially added potassium carbonate (0.253 g, 1.832 mmol), paraformaldehyde (0.275 g, 9.16 mmol) and tris(3,6-dioxaheptyl)amine (tda-1) (0.029 mL, 0.092 mmol). The reaction mixture was stirred at 85° C. for 10 h, then 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 by flash chromatography (0-40% EtOAc/hexanes) to give 36F (0.280 g, 0.723 mmol, 79% yield) as a colorless syrup, which solidified upon standing. MS (ESI) m/z: 388.3 [M+1]+. 1H NMR: (400 MHz, CDCl3) δ ppm 7.48 (1H, d, J=16.56 Hz), 7.20 (1H, d, J=8.28 Hz), 7.05-7.16 (1H, m), 6.63 (1H, br. s.), 6.22 (1H, s), 5.91 (1H, s), 4.55 (2H, s), 2.82 (3H, br. s.), 1.38-1.57 (18H, m).

Provenance & Evidence