Ammonium Chloride → 1-[4-(tert-Butyldiphenylsilyloxymethyl)-5-methyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazol-2-yl]ethanone

HRID 242388ノート

反応式

HRID 242388 の反応式
[Si:1]([O:18][CH2:19][C:20]1[N:21]=[CH:22][N:23]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[C:24]=1[CH3:25])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CON(C)[C:42](=[O:44])[CH3:43].[Cl-].[NH4+]>C1COCC1>[Si:1]([O:18][CH2:19][C:20]1[N:21]=[C:22]([C:42](=[O:44])[CH3:43])[N:23]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:32])([CH3:31])[CH3:33])[C:24]=1[CH3:25])([C:14]([CH3:16])([CH3:17])[CH3:15])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 537505N-Methoxy-N-methylacetamideHCID 710874044-(tert-butyldiphenylsilyloxymethyl)-5-methyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazoleHCID 178418339Butyllithium

生成物 1

HCID 710877791-[4-(tert-Butyldiphenylsilyloxymethyl)-5-methyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazol-2-yl]ethanone

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

4-(tert-Butyldiphenylsilyloxymethyl)-5-methyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazole (24.6 g) was dissolved in THF (300 mL), and cooled to −78° C. while stirring under an argon atmosphere. To the present solution was added dropwise n-butyl lithium (2.66 M hexane solution, 28.9 mL) slowly using a syringe, followed by stirring at the same temperature for 30 minutes. Then, N-methoxy-N-methylacetamide (10.5 mL) was added using a syringe, and stirring was continued for 2 hours while the temperature was raised to room temperature. A saturated aqueous ammonium chloride solution was added to the reaction solution to terminate the reaction, followed by extraction with ethyl acetate. The combined extract was washed with saturated brine, dried over anhydrous sodium sulfate, and subsequently the solvent was distilled off under reduced pressure. The resulting residue was purified by flash chromatography (ethyl acetate/hexane=0%→50%) using silica gel column (product name: Hi-Flash Column 5 L, manufactured by Yamazen Corporation) to afford the title compound (11.7 g).

後処理

  1. stirringby stirring at the same temperature for 30 minutes
  2. stirringstirring
  3. temperaturewas raised to room temperature
  4. customto terminate
  5. customthe reaction
  6. extractionfollowed by extraction with ethyl acetate
  7. extractionThe combined extract
  8. washwas washed with saturated brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationsubsequently the solvent was distilled off under reduced pressure
  11. customThe resulting residue was purified by flash chromatography (ethyl acetate/hexane=0%→50%)

出典と根拠

ORDレコード
ord-52ff34b703b04f81a0cbd681eaf6ba5f
出典データセット
uspto-grants-2014_02
特許番号
US08653126B2

反応ノート

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