Water → 2-(5-nitro-1H-indol-2-yl)propan-1-ol

HRID 468446ノート

反応式

HRID 468446 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N+:7]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH:19]([CH3:25])[C:20](OCC)=[O:21])=[CH:13]2)([O-:9])=[O:8].O.[OH-].[Na+]>C1COCC1>[N+:7]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14]([CH:19]([CH3:25])[CH2:20][OH:21])=[CH:13]2)([O-:9])=[O:8]

参加物

6

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59129193ethyl 2-(5-nitro-1H-indol-2-yl)propanoate

生成物 1

HCID 591293922-(5-nitro-1H-indol-2-yl)propan-1-ol収率 83.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a cooled solution of LiAlH4 (1.0 M in THF, 1.2 mL, 1.2 mmol) in THF (5.3 mL) at 0° C. was added a solution of ethyl 2-(5-nitro-1H-indol-2-yl)propanoate (0.20 g, 0.76 mmol) in THF (3.66 mL) dropwise. After addition, the mixture was allowed to warm up to room temperature and was stirred at room temperature for 3 h. The mixture was cooled to 0° C. Water (2 mL) was slowly added followed by careful addition of 15% NaOH (2 mL) and water (4 mL). The mixture was stirred at room temperature for 0.5 h and was then filtered through a short plug of celite using ethyl acetate. The organic layer was separated from the aqueous layer, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/1) to give 2-(5-nitro-1H-indol-2-yl)propan-1-ol (0.14 g, 81%).

後処理

  1. additionAfter addition
  2. temperatureThe mixture was cooled to 0° C
  3. stirringThe mixture was stirred at room temperature for 0.5 h
  4. filtrationwas then filtered through a short plug of celite
  5. customThe organic layer was separated from the aqueous layer
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/1)

出典と根拠

ORDレコード
ord-20094920d43142ccbe083d8d5e3c200f
出典データセット
uspto-grants-2014_01
特許番号
US08623905B2

反応ノート

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