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Acetonitrile → 3-Bromo-4-{4-[4-(tert-butyldimethylsilanyloxy)butyl]imidazol-1-ylmethyl}benzonitrile

HRID 923290
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HRID 923290 반응식
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[N:14]=[CH:15][N:16](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(#N)C.[Br:40][C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][C:48]=1[CH2:49]Br)[C:44]#[N:45]>C(OCC)(=O)C>[Br:40][C:41]1[CH:42]=[C:43]([CH:46]=[CH:47][C:48]=1[CH2:49][N:16]1[CH:17]=[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[N:14]=[CH:15]1)[C:44]#[N:45]
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참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 2884363-Bromo-4-(bromomethyl)benzonitrileHCID 668860904-[4-(tert-butyldimethylsilanyloxy)butyl]-1-trityl-1H-imidazole

생성물 1

HCID 668975903-Bromo-4-{4-[4-(tert-butyldimethylsilanyloxy)butyl]imidazol-1-ylmethyl}benzonitrile

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
40 °C

실험 절차

To 4-[4-(tert-butyldimethylsilanyloxy)butyl]-1-trityl-1H-imidazole (3.95 g, 7.95 mmol) is added acetonitrile (300 mL). To this solution is added 3-bromo-4-bromomethylbenzonitrile (2.14 g, 7.78 mmol). The solution is stirred at 40° C. for 18 h. The solvent is then removed in vacuo and methanol (300 ml) is added. The solution is heated to 55° C. and stirred for 1.5 h. Saturated sodium bicarbonate is then added and stirred for 10 min. The organic solvent is removed in vacuo, and the crude product extracted into ethyl acetate and washed with water. The organic solvent is removed in vacuo to give the crude product. Chromatography (silica gel, 1:0 to 1:1 to 0:1 hexanes:ethyl acetate) gives the pure product. MS (ESI) m/z 448, 450 (M+H).

후처리

  1. customThe solvent is then removed in vacuo and methanol (300 ml)
  2. additionis added
  3. temperatureThe solution is heated to 55° C.
  4. stirringstirred for 1.5 h
  5. additionSaturated sodium bicarbonate is then added
  6. stirringstirred for 10 min
  7. customThe organic solvent is removed in vacuo
  8. extractionthe crude product extracted into ethyl acetate
  9. washwashed with water
  10. customThe organic solvent is removed in vacuo
  11. customto give the crude product

출처 및 근거

ORD 기록
ord-a2fd5ea587f640c69f46d08d75e0cd3c
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09278969B2

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