碘甲烷 → N-[(4-Methoxyphenyl)methyl]-N-methylacetamide

反应方程式

[H-].[Na+].[CH3:3][O:4][C:5]1[CH:15]=[CH:14][C:8]([CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[CH:7][CH:6]=1.I[CH3:17]>>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]([CH3:17])[C:11](=[O:13])[CH3:12])=[CH:14][CH:15]=1

参与物

反应物 3

HCID 6328碘甲烷

HCID 24758氢化钠

HCID 37050N-(对甲氧基苄基)乙酰胺

产物 1

HCID 22660871N-[(4-Methoxyphenyl)methyl]-N-methylacetamide收率 90%

实验过程

Sodium hydride (60% in mineral oil) (1.11 grams, 27.4 mmol) was measured into a round bottom flask and triturated with hexanes. To this was added pure N-(4-methoxybenzyl)-acetamide (1.23 grams, 6.9 mmol) followed by iodomethane (1.95 grams, 13.7 mmol)and the resulting mixture stirred overnight. The reaction was filtered and the solvent removed under vacuum. The crude product was purified by flash column chromatography (SiO2, 2% EtOH in methylene chloride) to yield 1.2 grams of a colorless oil. HRMS (M+H) calcd for C11H16NO2: 194.1181; found: 194.1177. 1H NMR and 13C NMR show a mixture of rotamers at room temperature. 1H NMR (500 MHz, CDCl3) δ: 2.13 (s), 2.15 (s), 2.89 (s), 2.90 (s), 3.78 (s), 3.80 (s), 4.45 (s), 4.50 (s), 6.86 (m), 7.08 (d, J=9), 7.17 (d, J=9). 13C NMR (125 MHz, CDCl3) δ: 21.50, 21.91, 33.49, 35.33, 49.95, 53.72, 55.28, 113.95, 114.32, 127.66, 128.46, 129.44, 129.52, 158.95, 159.13, 170.63, 170.91.