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

HRID 748056ノート

反応式

HRID 748056 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

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 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 i 8 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.

後処理

  1. temperatureThe solution was slowly warmed to room temperature
  2. stirringstirred i 8 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

出典と根拠

ORDレコード
ord-90dc9990adc849ed83b9651920a2e860
出典データセット
uspto-grants-2008_07
特許番号
US07399778B2

反応ノート

読み込み中…