반응 #1134

반응 방정식

pyridine

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

cesium fluoride

→

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

수율 93.0%

용매

methanol

반응 조건

후처리

1. 1
   온도The stirred mixture was heated
2. 2
   온도at reflux for 18 h under inert atmosphere
3. 3
   온도After cooling the solvent
4. 4
   기타was removed in vacuo
5. 5
   workup.DISSOLUTIONthe resulting oil was dissolved in ethyl acetate (50 mL)
6. 6
   세척This was washed with water (20 mL), brine (20 mL)
7. 7
   건조dried (MgSO4)
8. 8
   농축concentrated
9. 9
   기타The crude material was chromatographed on "flash" silica gel with ethyl acetate:hexane (1:2 ) to 10% methanol

실험 절차

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).

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