Epichlorohydrin → HCID 86236611, compound

Participants

Reaction Steps

Reaction of 3′,4′-dimethoxy-7-hydroxy-flavone, 27 (6 g, 20 mol), 50% sodium hydride (2.4 g, 100 mmol) and epichlorohydrin (3.9 mL, 50 mmol) in dry dimethyl formamide (200 mL) using identical procedure as described for 28 furnished 33. Yield 5.3 g (74%); mp 148-149° C.; MS (FAB) 355 (M++1); IR (KBr) 1632; 1H NMR (200 MHz, CDCl3) δ 8.13 (d, J=9.5 Hz, 1H), 7.73 (dd, J=8.5 Hz, 2.0 Hz, 1H), 7.35 (d, J=1.9 Hz, 1H), 7.00 (dd, J=7.1 Hz, 2.3 Hz, 1H), 6.99 (d, J=2.2 Hz, 1H), 6.97 (d, J=8.5 Hz, 1H), 6.68 (s, 1H), 4.39 (dd, J=11.1 Hz, 2.9 Hz, 1H), 4.05 (dd, J=11.1 Hz, 5.8 Hz, 1H), 3.98 (s, 3H), 3.96 (s, 3H), 3.44-3.40 (m, 1H), 2.96 (t, J=4.5 Hz, 4.5 Hz, 1H), 2.81 (dd, J=4.8 Hz, 2.6 Hz, 1H).

Provenance & Evidence