反応 #626707

反応方程式

Hunig's base

150

1-Propargyl-3-methoxypyridine-2-one

phenylazide

→

white solid 151a

収率 92.0%

1-Phenyltriazolylmethyl-3-methoxypyridine-2-one

収率 92.0%

溶媒

THF

CH2Cl2

反応条件

後処理

1. 1
   workup.STIRRINGstirring
2. 2
   洗浄washed with 1:4 NH4OH/saturated NH4Cl (3×30 mL) and saturated NH4Cl (30 mL)
3. 3
   乾燥The organic layer was dried over Na2SO4
4. 4
   濃縮concentrated in vacuo
5. 5
   その他The crude product was triturated with hexanes

実験手順

150 (0.32 g, 1.951 mmol) and phenylazide (0.348 g, 2.926 mmol) were dissolved in anhydrous THF (10 mL) and stirred under argon at room temperature. Copper (I) iodide (0.011 g, 0.07 mmol) and Hunig's base (0.1 mL) were then added to the reaction mixture, and stirring continued for 4 h. The reaction mixture was diluted with CH2Cl2 (40 mL) and washed with 1:4 NH4OH/saturated NH4Cl (3×30 mL) and saturated NH4Cl (30 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was triturated with hexanes to give 510 mg (92%) of white solid 151a. 1H NMR (CDCl3, 400 MHz) δ 3.58 (3H, s), 5.11 (2H, s), 5.93 (1H, t, J=7.6), 6.42 (1H, d, J=7.2), 7.07 (1H, d, J=6.4), 7.16-7.20 (1H, m), 7.26 (2H, t, J=7.6), 7.49 (2H, d, J=8.0); 13C NMR (CDCl3, 100 MHz) δ 44.2, 55.2, 104.7, 112.0, 119.7, 121.8, 127.9, 128.1, 129.0, 136.2, 142.8, 149.3, 157.2. HRMS (EI) calcd for C15H14N4O2 [M]+ 282.1117. found 282.1115.

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