Methyl iodide → 4-Methoxydibenzofuran

反応式

[C:1](=O)([O-])[O-].[K+].[K+].CI.[CH:9]1[C:17]2[C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[O:14][C:13]=2[C:12]([OH:22])=[CH:11][CH:10]=1>CC(C)=O>[CH3:1][O:22][C:12]1[C:13]2[O:14][C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[C:17]=2[CH:9]=[CH:10][CH:11]=1

参加物

実験手順

Potassium carbonate (1.4 g, 10.11 mmol) and methyl iodide (0.42 mL, 6.74 mmol) were added to a solution of dibenzofuran-4-ol (1.24 g, 6.74 mmol) in acetone (65 mL). The reaction was heated at reflux and stirred for 18 h. Upon cooling, the reaction mixture was successively washed with 1 M sodium hydroxide, water and brine. The organic layer was dried on magnesium sulfate, filtered and then concentrated to give the product (1.33 g, 6.74 mmol, 100%) as a white needle that was used without further purification: Rf=0.37 (AcOEt-EP 1:19); mp: 49-50° C.; λmax (EtOH)/nm 279; IR (cm−1) 3054, 2839, 1900, 1633, 1496, 1451, 1423, 1330, 1309, 1267, 1188, 1089, 931, 893, 782, 737; 1H NMR, (300 MHz, CDCl3) δ 4.03 (3H, s, OCH3), 6.94 (1H, d, JH2-H3=8 Hz, H-3), 7.26 (1H, t, J=8 Hz), 7.36 (1H, t, J=7 Hz), 7.48 (1H, t, J=7 Hz), 7.54 (1H, d, J=7 Hz), 7.69 (1H, d, J=8 Hz), 7.94 (1H, d, J=8 Hz); 13C NMR, (75 MHz, CDCl3) δ 56.11 (OCH3), 109.31, 111.96, 112.82, 120.85, 122.86, 123.46, 124.43 (Cq), 125.72 (Cq), 127.21, 145.20 (Cq), 145.63 (Cq), 156.04 (Cq); MS (EI) m/z 199.1 M+; HRMS calcd for C13H10O2 [M+H]+ 199.0754, found 199.0754.