Cesium carbonate → 5-(2-methoxyethoxy)-1H-indole

HRID 1527183ノート

反応式

HRID 1527183 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:17][O:18][CH2:19][CH2:20]Br>CC(C)=O>[CH3:17][O:18][CH2:19][CH2:20][O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 160545-HydroxyindoleHCID 809722-Bromoethyl methyl ether

生成物 1

HCID 103525375-(2-methoxyethoxy)-1H-indole

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

5-hydroxyindole (5 g, 15 mmol) was dissolved in acetone (75 mL), cesium carbonate (5.38 g, 16.5 mmol) and 2-bromoethyl methyl ether (1.55 mL, 16.5 mmol) were added and the reaction mixture was stirred at reflux under nitrogen overnight. Acetone was concentrated. The residue was dissolved in water and extracted twice with EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 7/3) to give the desired material. TLC, Rf (c-hexane/EtOAc 1:1)=0.6; MS (LC-MS): 192.1 [M+H]+, 214.0 [M+Na]+, 405.1 [2M+Na]+; tR (HPLC conditions f): 1.56 min.

後処理

  1. temperatureat reflux under nitrogen overnight
  2. concentrationAcetone was concentrated
  3. dissolutionThe residue was dissolved in water
  4. extractionextracted twice with EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by flash column chromatography on silica gel (c-hexane to c-hexane/EtOAc 7/3)

出典と根拠

ORDレコード
ord-71222328413d4a1e9da2c81a9008df67
出典データセット
uspto-grants-2015_07
特許番号
US09085555B2

反応ノート

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