3-Pyridinecarboxaldehyde → Pyridin-3-yl(thiophen-2-yl)methanol

HRID 1720444

反応式

HRID 1720444 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[O:8])[CH:2]=1.[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[Li].CO.C(Cl)(Cl)Cl>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([OH:8])[C:10]2[S:9][CH:13]=[CH:12][CH:11]=2)[CH:2]=1

参加物

5

反応物 3

HCID 103713-PyridinecarboxaldehydeHCID 21584188Chloroform methanolHCID 178418439HCID 178418439、化合物

生成物 1

HCID 650499Pyridin-3-yl(thiophen-2-yl)methanol収率 62.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 3-pyridinecarboxaldehyde (5.0 mL, 53 mmol) in THF at -78° C. was added 2-thienyllithium (1.0M in THF, 64 mL, 64 mmol) and the reaction mixture was stirred for 2 hours at -78° C. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with ether. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo. Chromatography on silica gel (5%, then 10% methanol/CHCl3) gave 2-(3-pyridylhydroxymethyl)thiophene (6.30 g, 62% yield).

後処理

  1. customThe reaction mixture was quenched with saturated aqueous NH4Cl
  2. extractionextracted with ether
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-8f9a716072bd4c0bb8c2d6b1c9629c25
出典データセット
uspto-grants-1996_04
特許番号
US05506261

関連ノート

読み込み中…