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

HRID 44805ノート

反応式

HRID 44805 の反応式
[H-].[Na+].Cl.[NH:4]1[C:8]([C:9](=[O:11])[CH3:10])=[CH:7][CH:6]=[N:5]1.[CH3:12][Si:13]([CH3:20])([CH3:19])[CH2:14][CH2:15][O:16][CH2:17]Cl>C1COCC1>[CH3:12][Si:13]([CH3:20])([CH3:19])[CH2:14][CH2:15][O:16][CH2:17][N:4]1[C:8]([C:9](=[O:11])[CH3:10])=[CH:7][CH:6]=[N:5]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 27996231-(1H-pyrazol-5-yl)ethan-1-one hydrochloride

生成物 1

HCID 584059041-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)ethanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

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)+.

後処理

  1. temperatureAfter warming to rt over 1 h
  2. customThe reaction was quenched with water
  3. extractionextracted with EtOAc after 2 h
  4. customThe organic phase was collected
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customfollowed by purification by flash chromatography (silica, 50:50 EtOAc/hexane)

出典と根拠

ORDレコード
ord-3d94ce038bad4892a6741883f684aaab
出典データセット
uspto-grants-2013_09
特許番号
US08541418B2

反応ノート

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