3-(4-(Tert-butyldimethylsilyloxy)cyclohex-1-enyl)-2-fluoropyridine → 4-(2-Fluoropyridin-3-YL)cyclohex-3-enol

HRID 410235ノート

反応式

HRID 410235 の反応式
[Si]([O:8][CH:9]1[CH2:14][CH2:13][C:12]([C:15]2[C:16]([F:21])=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][CH2:10]1)(C(C)(C)C)(C)C>ClCCl>[F:21][C:16]1[C:15]([C:12]2[CH2:13][CH2:14][CH:9]([OH:8])[CH2:10][CH:11]=2)=[CH:20][CH:19]=[CH:18][N:17]=1

参加物

3

反応物 1

HCID 593268503-(4-(Tert-butyldimethylsilyloxy)cyclohex-1-enyl)-2-fluoropyridine

生成物 1

HCID 593267944-(2-Fluoropyridin-3-YL)cyclohex-3-enol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

To a flask containing 3-(4-(tert-butyldimethylsilyloxy)cyclohex-1-enyl)-2-fluoropyridine (1.5 g, 4.88 mmol) was added anhydrous dichloromethane (48.8 mL) under nitrogen. After cooling to 0° C., hydrogen fluoride-pyridine complex (1.696 mL, 19.51 mmol) was added dropwise. The reaction mixture was warmed to room temperature and stirred until the starting material had been consumed. The reaction mixture was quenched with saturated aqueous sodium bicarbonate and extracted with dichloromethane before drying over magnesium sulfate, filtering, and concentrating to a clear oil under reduced pressure. The material was used without purification.

後処理

  1. additionhydrogen fluoride-pyridine complex (1.696 mL, 19.51 mmol) was added dropwise
  2. temperatureThe reaction mixture was warmed to room temperature
  3. customhad been consumed
  4. customThe reaction mixture was quenched with saturated aqueous sodium bicarbonate
  5. extractionextracted with dichloromethane
  6. dry with materialbefore drying over magnesium sulfate
  7. filtrationfiltering
  8. concentrationconcentrating to a clear oil under reduced pressure
  9. customThe material was used without purification

出典と根拠

ORDレコード
ord-a00f4a71f3c945fe8f544cfc85816f4d
出典データセット
uspto-grants-2014_06
特許番号
US08759532B2

反応ノート

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