تفاعل #73083

معادلة التفاعل

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

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter warming to rt over 1 h
2. 2
   أخرىThe reaction was quenched with water
3. 3
   استخلاصextracted with EtOAc after 2 h
4. 4
   أخرىThe organic phase was collected
5. 5
   تجفيفdried with sodium sulfate
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated under reduced pressure
8. 8
   أخرىfollowed by purification by flash chromatography (silica, 50:50 EtOAc/hexane)

الإجراء التجريبي

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)+.

المصدر