反応 #73083

反応方程式

2-(trimethylsilyl)ethoxymethyl chloride

sodium hydride

1-(1H-pyrazole-5-yl)ethan-1-one hydrochloride

→

1-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)ethanone

溶媒

THF

THF

反応条件

後処理

1. 1
   温度After warming to rt over 1 h
2. 2
   その他The reaction was quenched with water
3. 3
   抽出extracted with EtOAc after 2 h
4. 4
   その他The organic phase was collected
5. 5
   乾燥dried with sodium sulfate
6. 6
   ろ過filtered
7. 7
   濃縮concentrated under reduced pressure
8. 8
   その他followed by purification by flash chromatography (silica, 50:50 EtOAc/hexane)

実験手順

To a suspension of sodium hydride (3.07 g, 76.75 mmol) in 100 mL of anhydrous THF cooled to 0° C. under N2 (g) inlet was added 1-(1H-pyrazole-5-yl)ethan-1-one hydrochloride (3.09 g, 21.08 mmol). After warming to rt over 1 h, a solution of 2-(trimethylsilyl)ethoxymethyl chloride (4.5 mL, 25.43 mmol) in 100 mL of anhydrous THF was added to the reaction flask via cannulation. The reaction was quenched with water and extracted with EtOAc after 2 h. The organic phase was collected, dried with sodium sulfate, filtered and concentrated under reduced pressure followed by purification by flash chromatography (silica, 50:50 EtOAc/hexane) to give 1-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)ethanone. LCMS; 241.1 m/z (M+H)+.

出典