Dimethylformamide → 4-Iodo-1-phenethyl-imidazole-2-carbaldehyde

HRID 1773857ノート

反応式

HRID 1773857 の反応式
[I:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=1.[Li+].CC([N-]C(C)C)C.CN([CH:26]=[O:27])C>C1COCC1>[I:1][C:2]1[N:3]=[C:4]([CH:26]=[O:27])[N:5]([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 2724682Lithium diisopropylamideHCID 867039464-Iodo-1-phenethyl-imidazole

生成物 1

HCID 867039454-Iodo-1-phenethyl-imidazole-2-carbaldehyde

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 4-iodo-1-phenethyl-imidazole (example 2C) (563 mg, 1.89 mmoles) in THF (13 mL) under argon is cooled to −78° C. A 2.0M LDA solution (1.04 mL, 2.08 mmoles) is added dropwise. After 30 minutes at −78° C., DMF (161 μL, 2.08 mmoles) is added dropwise. The reaction mixture is allowed to reach 0° C., then it is quenched by adding a half-saturated NaHCO3 solution. The aqueous phase is extracted three times with AcOEt. The organic phase is washed with water, brine, dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel chromatography using (heptane:AcOEt) as eluent with a gradient from (95:5) to (70:30) to give 4-iodo-1-phenethyl-imidazole-2-carbaldehyde.

後処理

  1. customto reach 0° C.
  2. customit is quenched
  3. additionby adding a half-saturated NaHCO3 solution
  4. extractionThe aqueous phase is extracted three times with AcOEt
  5. washThe organic phase is washed with water, brine
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent is removed under reduced pressure
  9. customThe residue is purified by silica gel chromatography

出典と根拠

ORDレコード
ord-407e33423cf54d29bee1299849f41be2
出典データセット
uspto-grants-2016_02
特許番号
US09255101B2

反応ノート

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