反应详情

温度

25 °C

To a 0.275 g (11.0 mmol) of pre-washed (with distilled diethyl ether) sodium hydride under argon were added 1.00 g (4.80 mmol) of 1,4-dihydroxyanthracene, 0.75 mL (12.0 mmol) of iodomethane, and 10 mL of DMF (distilled over CaH2). The solution was stirred at 25° C. for 1.5 h, diluted with 20 mL of water, and acidified with 6 N HCl (pH ˜2). The mixture was extracted three times with ethyl acetate, and the combined extract was washed twice with water, and brine, dried (MgSO4), concentrated to give 1.07 g (94% yield) of compound 2. Recrystallization from ether:hexane (1:1) gave 0.89 g (78% yield) of yellow solids: mp 132-133° C. (Lit.6 134-136° C.); MS, FAB, m/z 239 (M+1), 238 (M+); 1H NMR d 8.70 (s, 2H, C9,10H), 7,97 (dd, J=6.1, 3.6 Hz, 2H, C5,8H), 7.40 (dd, J=6.6, 3.2 Hz, 2H, C6,7H ), 6.55 (s, 2H, C2,3H), 3.97 (s, 6H, OCH3); 13C NMR d 149.5 (s, C8a,10a), 131.5 (s, C4a,9a), 128.5 (d, C9,10), 125.5 (d, C5,8), 120.7 (d, C6,7), 100.9 (d, C2,3), 55.6 (s, OCH3).

1. washTo a 0.275 g (11.0 mmol) of pre-washed (with distilled diethyl ether) sodium hydride under argon
2. extractionThe mixture was extracted three times with ethyl acetate
3. extractionthe combined extract
4. washwas washed twice with water, and brine
5. dry with materialdried (MgSO4)
6. concentrationconcentrated