反応 #8600

反応方程式

4-chloro-2-picoline

ethyl 4-fluorobenzoate

lithium bis(trimethylsilyl)amide

→

2-(4-chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone

収率 99.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他over 30 minutes
2. 2
   workup.ADDITIONUpon complete addition
3. 3
   その他the cold bath was removed
4. 4
   濃縮The reaction mixture was concentrated under reduced pressure and methanol
5. 5
   workup.ADDITIONwas added to the reaction
6. 6
   その他resulting in the formation of a white precipitate
7. 7
   ろ過The precipitate was collected by filtration
8. 8
   その他dried

実験手順

To a cold (0 ° C.) solution of 4-chloro-2-picoline (5.0 g,39 mmol) and ethyl 4-fluorobenzoate (6.6 g, 39 mmol) in tetrahydrofuran (100 mL) was added lithium bis(trimethylsilyl)amide (80 mL, 1.0 M in tetrahydrofuran, 80 mmol) dropwise via a pressure equalizing funnel over 30 minutes. Upon complete addition, the cold bath was removed and the resulting solution was stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure and methanol was added to the reaction, resulting in the formation of a white precipitate. The precipitate was collected by filtration and dried to give 2-(4-chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone (9.6 g, 99%) as a white solid. 1H-NMR (DMSO-d6): δ 7.90 (m, 3H), 7.11 (t, 2H), 6.56 (s,1 H), 5.67 (s, 1 H), 4.14 (m, 2H); 19F-NMR (DMSO-d6): δ −115.67; MS m/z 250 (M+1).

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