2-Ethylbutyraldehyde → HCID 68593352、化合物

HRID 748067ノート

反応式

HRID 748067 の反応式
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[CH2:18]([CH:20]([CH2:23][CH3:24])[CH:21]=[O:22])[CH3:19].[NH4+].[Cl-]>CCOCC>[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH:21]([OH:22])[CH:20]([CH2:23][CH3:24])[CH2:18][CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 73592-EthylbutyraldehydeHCID 25517Ammonium ChlorideHCID 779181-BenzylimidazoleHCID 178418339Butyllithium

生成物 1

HCID 68593352HCID 68593352、化合物収率 69%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-78 °C

実験手順

To a chilled reaction vessel at −45° C. containing 1-benzyl-1H-imidazole (3.0 g, 19.0 mmol) in Et2O (100 mL) was added a solution of n-butyllithium (2.5M in hexanes, 10.8 mL, 26.9 mmol) dropwise. After 30 min, the reaction vessel was cooled to −78° C. and 2-ethylbutyraldehyde (2.8 mL, 22.8 mmol) was added dropwise. The reaction mixture was warmed to 0° C. and stirred for 15 min, then poured into sat. aqueous NH4Cl and extracted with Et2O. The organic layer was washed with H2O, dried over MgSO4, filtered and concentrated in vacuo. The resulting yellow oil was purified by column chromatography (SiO2, EtOAc/hexane, 3:2, then 7:3) to yield a clear oil in 69% yield.

後処理

  1. customTo a chilled reaction vessel at −45° C.
  2. temperatureThe reaction mixture was warmed to 0° C.
  3. extractionextracted with Et2O
  4. washThe organic layer was washed with H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resulting yellow oil was purified by column chromatography (SiO2, EtOAc/hexane, 3:2
  9. custom7:3) to yield a clear oil in 69% yield

出典と根拠

ORDレコード
ord-22ef515c1a0e407fae3abea73fd0f058
出典データセット
uspto-grants-2008_07
特許番号
US07399778B2

反応ノート

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