3-Methoxyxanthone → HCID 14966062, compound

Participants

Reaction Steps

To a suspension of lithium aluminum hydride (0.524 g, 13.8 mmole) in Et2O (30 ml) at 0° was added, dropwise, a solution of xanthone 8 (1 g, 4.42 mmole) in toluene (25 ml). The resulting mixture was stirred at room temperature for 30 min, then refluxed vigorously for 17 hrs. After cooling in an ice bath, the reaction was quenched carefully with EtOAc (1.5 ml), MeOH (1.5 ml) and finally with dilute HCl solution until the aqueous layer was acidic. The reaction mixture was partitioned between 10% EtOAc-hexanes and water. After the organic layer was separated, the aqueous layer was extracted two more times with 10% EtOAc-hexanes. The combined organic layers were washed with saturated NaCl solution, dried over anhydrous Na2SO4 and filtered through a silica gel plus. After concentration of the filtrate, 3-methoxy-9H-xanthene 9 (0.806 g, 86%) was isolated as a slightly yellow solid: m.p. 72-74° C.; 1H NMR (CDCl3): delta 7.13-7.20 (2H, m), 6.98-7.06 (3H, m), 6.58-6.62 (2H, m), 3.97 (2H, s) and 3.79 (3H, s); 1R (CHCl3): 3000, 2935, 2836, 1625, 1596, 1520, 1480, 1455, 1438, 1275, 1227, 1150, 1119, 1092, 1031, 962 and 837 cm-1.

Provenance & Evidence