Ethanol → Ethyl indole-5-carboxylate

HRID 1371921ノート

反応式

HRID 1371921 の反応式
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([OH:3])=[O:2].C(N1C=CN=C1)(N1[CH:19]=[CH:18]N=C1)=O.CCO.[H-].[Na+]>C1COCC1>[CH2:18]([O:2][C: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])[CH3:19]

参加物

6

反応物 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 742801H-Indole-5-Carboxylic Acid

生成物 1

HCID 10987040Ethyl indole-5-carboxylate収率 127.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Combine 5-carboxyindole (4.8 g, 29.8 mmol) in 150 mL THF and carbonyldiimidazole (9.7 g, 59.6 mmol) and stir overnight at ambient temperature. Treat the reaction mixture with 25 mL EtOH and 1.2 g (29.8 mmol) of a 60% oil dispersion of NaH and stir for 2 hours. Concentration under vacuum gives a residue. Partition the residue between 150 mL EtOAc and 100 mL brine. Separate the layers, dry the organic layer over MgSO4, filter, and concentrated to an oil. Chromatograph on silica gel eluting with 1% MeOH in CHCl3 to give 7.2 g of an oil. Crystallize the oil from toluene gives the title compound: Analysis for C11H11NO2: calcd: C, 69.83; H, 5.86; N, 7.40; found: C, 69.82; H, 5.90; N, 7.38; ISMS 190 (M+1).

後処理

  1. concentrationConcentration under vacuum
  2. customgives a residue
  3. customPartition the residue between 150 mL EtOAc and 100 mL brine
  4. customSeparate the layers
  5. dry with materialdry the organic layer over MgSO4
  6. filtrationfilter
  7. concentrationconcentrated to an oil

出典と根拠

ORDレコード
ord-20deb848a7f44fc5a49a3be32c12cfdc
出典データセット
uspto-grants-2007_01
特許番号
US07157488B2

反応ノート

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