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

HRID 1773857노트

반응식

HRID 1773857 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-407e33423cf54d29bee1299849f41be2
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255101B2

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