반응 #73083

반응 방정식

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

용매

THF

THF

반응 조건

후처리

1. 1
   온도After warming to rt over 1 h
2. 2
   기타The reaction was quenched with water
3. 3
   추출extracted with EtOAc after 2 h
4. 4
   기타The organic phase was collected
5. 5
   건조dried with sodium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated under reduced pressure
8. 8
   기타followed by purification by flash chromatography (silica, 50:50 EtOAc/hexane)

실험 절차

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)+.

출처