反応 #1141

反応方程式

5-(2-Hydroxy-2-methyl-3-butynyl)-3-(1-methyl-5-pyrrolidin-2-onyl)pyridine

sodium hydride

toluene acetone

→

5-ethynyl-3-(1-methyl-5-pyrrolidin-2-onyl)pyridine

収率 81.1%

溶媒

toluene

反応条件

後処理

1. 1
   その他were removed by distillation
2. 2
   workup.ADDITIONwater (10 mL) and ethyl acetate (20 mL) were added
3. 3
   その他The organic phase was separated
4. 4
   抽出the aqueous layer extracted with ethyl acetate (2×20 mL)
5. 5
   洗浄the combined organic extracts were washed with brine (10 mL)
6. 6
   乾燥dried (MgSO4)
7. 7
   濃縮concentrated in vacuo
8. 8
   その他The crude product was purified by silica gel column chromatography with ethyl acetate as eluant

実験手順

5-(2-Hydroxy-2-methyl-3-butynyl)-3-(1-methyl-5-pyrrolidin-2-onyl)pyridine (200 mg, 0.77 mmol) was dissolved in toluene (20 mL) and catalytic sodium hydride (5 mg) was added. The solution was heated until several milliliters of toluene-acetone mixture were removed by distillation. The mixture was cooled to 25° C. and water (10 mL) and ethyl acetate (20 mL) were added. The organic phase was separated and the aqueous layer extracted with ethyl acetate (2×20 mL) and the combined organic extracts were washed with brine (10 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by silica gel column chromatography with ethyl acetate as eluant to afford 5-ethynyl-3-(1-methyl-5-pyrrolidin-2-onyl)pyridine as a solid (125 mg, 81%). M.p. 83°-84° C.; 1H NMR (CDCl3, 300 MHz): δ 8.69 (d, J=2 Hz, 1H), 8.46 (d, J=2 Hz, 1H), 7.62 (t, J=2 Hz, 1H), 4.57 (dd, J=7, 6 Hz, 1H), 3.28 (s, 1H), 2.70 (s, 3H), 2.45-2.65 (m, 3H), 1.88 (m, 1H).

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