反応 #7231

反応方程式

3-bromoquinoline

sodium methoxide

→

3-methoxyquinoline

収率 6.2%

溶媒

DMF

反応条件

後処理

1. 1
   濃縮The reaction mixture was then concentrated
2. 2
   その他The organic phase was separated
3. 3
   洗浄washed with brine (2×60 mL)
4. 4
   乾燥dried (MgSO4)
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   その他purified by column chromatography on silica gel (ethyl acetate/hexane; 1:3)

実験手順

A solution of 3-bromoquinoline (22.54 g, 108 mmol) in anhydrous DMF (110 mL) was treated with sodium methoxide (11.70 g, 217 mmol) and stirred at 80° C. for 16 hours. The reaction mixture was then concentrated and the residue taken up in ethyl acetate (300 mL) and water (60 mL). The organic phase was separated, washed with brine (2×60 mL), dried (MgSO4), filtered, concentrated and purified by column chromatography on silica gel (ethyl acetate/hexane; 1:3) to give 3-methoxyquinoline (1.06 g, 6%). 1H NMR (CDCl3) δ 3.95 (s, 3H), 7.38 (d, 1H, J=1.5 Hz), 7.54 (m, 2H), 7.72 (d, 1H, J=7.5 Hz), 8.04 (d, 1H, J=7.5 Hz), 8.67 (d, 1H, J=1.5 Hz).

出典