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

HRID 1720444

반응식

HRID 1720444 반응식
[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

참가 물질

5

반응물 3

HCID 103713-PyridinecarboxaldehydeHCID 21584188Chloroform methanolHCID 178418439HCID 178418439, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8f9a716072bd4c0bb8c2d6b1c9629c25
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05506261

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