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

HRID 1877971
ノート
印刷プレビュー

反応式

HRID 1877971 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
40 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2261d0b090094bfeb3f68cecf8145855
出典データセット
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08314097B2

反応ノート

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