Ethyl 1H-indole-3-acetate → Ethyl (2,3-dihydro-1H-indol-3-yl)acetate

HRID 1174526ノート

反応式

HRID 1174526 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:2]1.C([BH3-])#N.[Na+]>C(O)(=O)C.[OH-].[Na+].ClCCl>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[NH:1][CH2:2]1)[CH3:15]

参加物

6

反応物 2

HCID 13067Ethyl 1H-indole-3-acetateHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 21795444Ethyl (2,3-dihydro-1H-indol-3-yl)acetate収率 78.9%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

Ethyl indole-3-acetate (4 g, 19 mmol, 98%) was taken up in acetic acid (40 cm3) and sodium cyanoborohydride (4 g, 63 mmol) was added. The reaction was stirred at room temperature for 2 h, then diluted with aqueous sodium hydroxide until basic. The aqueous mixture was extracted with ethyl acetate and the organic layer was separated, dried and concentrated to dryness under reduced pressure. The solid obtained was taken up in dichloromethane and chromatographed on silica eluting with dichloro-methane with increasing volumes of methanol. The product containing fractions were combined and concentrated to yield ethyl-2,3-dihydro-indole-3-acetate as a solid (3 g, 15 mmol, 78%).

後処理

  1. extractionThe aqueous mixture was extracted with ethyl acetate
  2. customthe organic layer was separated
  3. customdried
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe solid obtained
  6. customchromatographed on silica eluting with dichloro-methane with increasing volumes of methanol
  7. additionThe product containing fractions
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-b1af29fb948e4562a68bb36c89d0be54
出典データセット
uspto-grants-2010_11
特許番号
US07838518B2

反応ノート

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