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

HRID 242382
ノート
印刷プレビュー

反応式

HRID 242382 の反応式
[Si:1]([O:18][CH2:19][C:20]1[N:21]=[CH:22][N:23]([CH2:25][CH:26]=[CH2:27])[CH:24]=1)([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:36](=[O:38])[CH3:37].[Cl-].[NH4+]>C1COCC1>[Si:1]([O:18][CH2:19][C:20]1[N:21]=[C:22]([C:36](=[O:38])[CH3:37])[N:23]([CH2:25][CH:26]=[CH2:27])[CH:24]=1)([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
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

6

反応物 4

HCID 25517Ammonium ChlorideHCID 537505N-Methoxy-N-methylacetamideHCID 892621944-(tert-Butyldiphenylsilyloxymethyl)-1-(2-propenyl)-1H-imidazoleHCID 178418339Butyllithium

生成物 1

HCID 892622101-[4-(tert-Butyldiphenylsilyloxymethyl)-1-(2-propenyl)-1H-imidazol-2-yl]ethanone

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒

反応条件

温度
-78 °C

実験手順

The compound (1.26 g) obtained in (1) was dissolved in THF (50 mL), and cooled to −78° C. while stirring under nitrogen stream. To the present solution was added dropwise n-butyl lithium (2.76 M hexane solution, 1.82 mL), followed by stirring at the same temperature for 30 minutes. Then, N-methoxy-N-methylacetamide (1.05 mL) was added, and stirring was continued for 30 minutes. A saturated aqueous ammonium chloride solution was added to the reaction solution to terminate the reaction, followed by extraction with ethyl acetate. The 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=5%→70%) using silica gel column (product name: Hi-Flash Column 3 L, manufactured by Yamazen Corporation) to afford the title compound (0.75 g).

後処理

  1. stirringby stirring at the same temperature for 30 minutes
  2. stirringstirring
  3. customto terminate
  4. customthe reaction
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe extract was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationsubsequently the solvent was distilled off under reduced pressure
  9. customThe resulting residue was purified by flash chromatography (ethyl acetate/hexane=5%→70%)

出典と根拠

ORDレコード
ord-4470891a37844a9a996a6b0a55a1f76c
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08653126B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート