Chloromethyl Methyl Ether → 2-(4-(benzyloxy)-3-(methoxymethoxy)phenyl)-3,7-bis(methoxymethoxy)-4H-chromen-4-one

Participants

Reaction Steps

To 2-(4-(benzyloxy)-3-(methoxymethoxy)phenyl)-3-hydroxy-7-(methoxymethoxy)-4H-chromen-4-one (55 mg, 0.12 mmol) in 2 mL of DCM was added DIPEA (31 mg, 0.24 mmol), followed by slow addition of chloro(methoxy)methane (15 mg, 0.18 mmol). The reaction mixture was stirred at rt under Ar atmosphere for 3 h and diluted with ether (30 mL). It was washed with water (3×30 mL) and dried over MgSO4 and concentrated. The crude product was purified with silica chromatography (hexane/EtOAc) to afford 2-(4-(benzyloxy)-3-(methoxymethoxy)phenyl)-3,7-bis(methoxymethoxy)-4H-chromen-4-one as a white solid (55 mg, 90%). 1H NMR (400 MHz, CDCl3) δ 8.14 (d, J=8.8 hz, 1H), 7.91 (d, J=2.0 Hz, 1H), 7.71 (dd, J=8.4 Hz, 2.0 Hz, 1H), 7.46-7.44 (m, 2H), 7.39 (m, 2H), 7.34-7.31 (m, 1H), 7.12 (d, J=2.4 Hz, 1H), 7.05 (dd, J=8.8, 2.4 Hz, 1H), 7.03 (d, J=8.4 Hz, 1H), 5.30 (s, 2H), 5.28 (s, 2H), 5.24 (s, 2H), 5.21 (s, 2H), 3.55 (s, 3H), 3.51 (s, 3H), 3.18 (s, 3H); MS (ESI) m/z 509 (M+H+).

Provenance & Evidence