Hexane → 2-(5-Nitro-indol-1-yl)-3-phenyl-propionic acid methyl ester

HRID 2245510ノート

反応式

HRID 2245510 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:19][O:20][C:21](=[O:38])[CH:22](OS(C(F)(F)F)(=O)=O)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CCCCCC>CC(C)=O.CCOC(C)=O>[CH3:19][O:20][C:21](=[O:38])[CH:22]([N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH:7]=[CH:8]1)[CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

参加物

7

反応物 4

HCID 8058HexaneHCID 10796Cesium carbonateHCID 225235-NitroindoleHCID 13388932alpha-(Trifluoromethylsulfonyloxy)hydrocinnamic acid methyl ester

生成物 1

HCID 592167062-(5-Nitro-indol-1-yl)-3-phenyl-propionic acid methyl ester

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To 5-nitro-1H-indole (5.18 g, 31.93 mmol) in acetone (200 ml) at ambient temperature under a nitrogen atmosphere was added cesium carbonate (21.80 g, 67.06 mmol) followed by 3-phenyl-2-trifluoromethanesulfonyloxy-propionic acid methyl ester (10.96 g, 35.13 mmol). The resulting dark red mixture was stirred for 5 hours, concentrated in vacuo to a brown powder which was then partitioned between H2O (100 ml) and EtOAc (300 ml). All organics were combined, extracted with brine (250 ml), dried with MgSO4, filtered, and concentrated in vacuo. Gradient SiO2 chromatography (Hexane:EtOAc) afforded 2-(5-nitro-indol-1-yl)-3-phenyl-propionic acid methyl ester as an opaque syrup (5.91 g, 57% yield): MS (ESI) m/z 325, MS (ESI) m/z 323.

後処理

  1. concentrationconcentrated in vacuo to a brown powder which
  2. customwas then partitioned between H2O (100 ml) and EtOAc (300 ml)
  3. extractionextracted with brine (250 ml)
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e44e252b26d04892bc29f7c29ccd6f71
出典データセット
uspto-grants-2010_03
特許番号
US07683091B2

反応ノート

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