反応 #1134

反応方程式

pyridine

5-(4-tert-butyldimethylsilyloxyphenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine

cesium fluoride

→

5-(4-hydroxyphenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine

収率 93.0%

溶媒

methanol

反応条件

後処理

1. 1
   温度The stirred mixture was heated
2. 2
   温度at reflux for 18 h under inert atmosphere
3. 3
   温度After cooling the solvent
4. 4
   その他was removed in vacuo
5. 5
   workup.DISSOLUTIONthe resulting oil was dissolved in ethyl acetate (50 mL)
6. 6
   洗浄This was washed with water (20 mL), brine (20 mL)
7. 7
   乾燥dried (MgSO4)
8. 8
   濃縮concentrated
9. 9
   その他The crude material was chromatographed on "flash" silica gel with ethyl acetate:hexane (1:2 ) to 10% methanol

実験手順

The above-described pyridine derivative (750 mg, 2.04 mmol) was dissolved in methanol (40 mL) and cesium fluoride (620 mg, 4.08 mmol) was added. The stirred mixture was heated at reflux for 18 h under inert atmosphere. After cooling the solvent was removed in vacuo and the resulting oil was dissolved in ethyl acetate (50 mL). This was washed with water (20 mL), brine (20 mL), dried (MgSO4) and concentrated. The crude material was chromatographed on "flash" silica gel with ethyl acetate:hexane (1:2 ) to 10% methanol: ethyl acetate as eluant to afford 5-(4-hydroxyphenyl)-3-(1-methyl-2-pyrrolidinyl)pyridine 480 mg, 93% as a colorless foam, 1H NMR (CDCl3, 300 MHz): δ 8.66 (d, J=2 Hz, 1 H), 8.43 (d, J=2 Hz, 1 H), 7.90 (s, 1 H), 7.32 (d, J=9 Hz, 2 H), 6.81 (d, J=9 Hz, 2 H), 3.33 (t, J=8 Hz, 1 H), 3.22 (t, J=8 Hz, 1 H), 2.41 (m, 1 H), 2.28 (s, 3 H), 2.10 (m, 2 H), 1.93 (m, 2 H).

出典