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

HRID 52182

反応式

HRID 52182 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-821002a002e645fc8b3d520076f6a82a
出典データセット
uspto-grants-1997_04
特許番号
US05616596

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