4-(Imidazol-1-ylmethyl)benzonitrile → 4-[3-(Tert-butyl-dimethyl-silanyloxy)-1-imidazol-1-yl-propyl]-benzonitrile

HRID 1421777노트

반응식

HRID 1421777 반응식
[N:1]1([CH2:6][C:7]2[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:25]([Si:29]([O:32][CH2:33][CH2:34]I)([CH3:31])[CH3:30])([CH3:28])([CH3:27])[CH3:26]>C1COCC1>[C:25]([Si:29]([CH3:31])([CH3:30])[O:32][CH2:33][CH2:34][CH:6]([C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][CH:8]=1)[N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1)([CH3:28])([CH3:27])[CH3:26]

참가 물질

5

반응물 3

HCID 12364494-(Imidazol-1-ylmethyl)benzonitrileHCID 2733832Lithium HexamethyldisilazideHCID 11129873tert-Butyl(2-iodoethoxy)dimethylsilane

생성물 1

HCID 187797914-[3-(Tert-butyl-dimethyl-silanyloxy)-1-imidazol-1-yl-propyl]-benzonitrile

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

반응 조건

온도
-60 °C

실험 절차

4-Imidazol-1-ylmethyl-benzonitrile (5.5 gms, 30 mmol) was suspended in freshly distilled THF (150 mL) in dry glassware and stirred under argon in a -60° C. dry ice acetone bath then Lithium bis(trimethylsilyl)amide 1 molar in THF (33 mL) was added slowly. The mixture was stirred for 30 minutes and the temperature was reduced to -78° C. A suspension of tert-butyl-(2-iodo-ethoxy)-dimethyl-silane (9.5 gm, 33 mmol) in 20 mL of THF was cooled to -78° C. and added via cannula to the first solution and the resulting mixture was allowed to slowly warm to ambient temperature. After 16 hours the reaction was quenched by the addition of 10 mL of water and the solvent was removed in vacuo. The residue was suspended in ethyl acetate (200 mL) and extracted 2 times with saturated aqueous sodium bicarbonate (100 mL), then water (100 mL), then saturated sodium chloride solution (100 mL). The organic solvent was removed in vacuo and the residue was chromatographed on silica gel using 1:3 ethyl acatate: hexanes. The desired fractions were combined and the solvent was removed in vacuo to give the desired product.

후처리

  1. stirringThe mixture was stirred for 30 minutes
  2. customwas reduced to -78° C
  3. temperaturewas cooled to -78° C.
  4. additionadded via cannula to the first solution
  5. temperatureto slowly warm to ambient temperature
  6. customAfter 16 hours the reaction was quenched by the addition of 10 mL of water
  7. customthe solvent was removed in vacuo
  8. extractionextracted 2 times with saturated aqueous sodium bicarbonate (100 mL)
  9. customThe organic solvent was removed in vacuo
  10. customthe residue was chromatographed on silica gel using 1:3 ethyl acatate
  11. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-dfbc56d7391e4eeb87e18c046856992b
출처 데이터셋
uspto-grants-2000_06
특허 번호
US06077853

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