Dimethylformamide → HCID 57683735, compound

Participants

Reaction Conditions

Reaction Steps

6-Bromo-4-hydroxycoumarin (1.19 mmol, 0.287 g), K2CO3 (3.57 mmol, 0.493 g) and 2-3-(bromopropoxy)tetrahydro-2H-pyran (1.19 mmol, 0.264 g) is suspended in 10 mL of acetone, and is heated to 55° C. for 24 hrs at which time the reaction is not complete. Cs2CO3 (1.54 mmol, 0.5 g) and 5 mL of DMF are added and the reaction is heated for an additional 2 hrs. Twenty-five percent of the crude THP protected material is purified by HPLC to afford the title compound (70.8 mg, 62%); 1H NMR (CDCl3, 300 MHz) δ 7.91 (1H, d, J=2.25 Hz), 7.82 (1H, dd, J=2.5, 9 Hz), 7.39 (1H, d, J=9 Hz), 5.98 (1H, s), 4.59 (1H, m), 4.31 (2H, t, J=6 Hz), 3.83 (1H, m), 3.72 (1H, m), 3.55 (2H, m), 2.09 (2H, m), 1.65 (2H, m), 1.45 (4H, m); MS (ESI, Pos.) calcd for C17H19BrO5 m/z [M+H]=383.0, found 383.1.

Provenance & Evidence