2-Ethylbutyraldehyde → 2-Ethyl-1-[1-(4-fluorobenzyl)-1H-1,2,4-triazol-5-yl]butan-1-ol

HRID 2243134

반응식

HRID 2243134 반응식
[F:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][N:7]2[CH:11]=[N:10][CH:9]=[N:8]2)=[CH:4][CH:3]=1.C([Li])CCC.[CH2:19]([CH:21]([CH2:24][CH3:25])[CH:22]=[O:23])[CH3:20]>C1COCC1>[CH2:19]([CH:21]([CH2:24][CH3:25])[CH:22]([C:11]1[N:7]([CH2:6][C:5]2[CH:12]=[CH:13][C:2]([F:1])=[CH:3][CH:4]=2)[N:8]=[CH:9][N:10]=1)[OH:23])[CH3:20]

참가 물질

5

반응물 3

HCID 73592-EthylbutyraldehydeHCID 232736751-(4-Fluorobenzyl)-1H-1,2,4-triazoleHCID 178418339Butyllithium

생성물 1

HCID 685941182-Ethyl-1-[1-(4-fluorobenzyl)-1H-1,2,4-triazol-5-yl]butan-1-ol수율 47%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a stirred solution of 1-(4-fluorobenzyl)-1H-1,2,4-triazole (0.500 g, 2.82 mmol) in THF (30 mL) at −78° C. was added a solution of n-butyllithium (2.5M in hexanes, 1.1 mL, 2.9 mmol) dropwise. The mixture was stirred at −78° C. for 1.5 h, then 2-ethylbutyraldehyde (0.42 mL, 3.4 mmol) was added. The solution was slowly warmed to room temperature and stirred 18 h. It was then quenched with saturated aqueous NH4Cl and extracted twice with EtOAc. The organic extracts were dried (MgSO4), filtered, concentrated in vacuo and purified by column chromatography (SiO2, EtOAc/hexane, 1:1) to yield an oil in 47% yield.

후처리

  1. temperatureThe solution was slowly warmed to room temperature
  2. stirringstirred 18 h
  3. customIt was then quenched with saturated aqueous NH4Cl
  4. extractionextracted twice with EtOAc
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified by column chromatography (SiO2, EtOAc/hexane, 1:1)
  9. customto yield an oil in 47% yield

출처 및 근거

ORD 기록
ord-1daf8aca97b0450ba554b98204b4f6d9
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07674813B2

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