Sodium Hydroxide → 3-acetyl-1-butyl-1H-indole-6-carboxylic acid

HRID 14223

反応式

HRID 14223 の反応式
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([O:15]C)=[O:14])=[CH:10][CH:11]=2)[N:6]([CH2:17][CH2:18][CH2:19][CH3:20])[CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([OH:15])=[O:14])=[CH:10][CH:11]=2)[N:6]([CH2:17][CH2:18][CH2:19][CH3:20])[CH:5]=1)(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 14798Sodium Hydroxide2 回HCID 21086157methyl 3-acetyl-1-butyl-1H-indole-6-carboxylate

生成物 1

HCID 210857003-acetyl-1-butyl-1H-indole-6-carboxylic acid収率 84.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

Methyl 3-acetyl-1-butyl-1H-indole-6-carboxylate (2.00 g) was dissolved in methanol (100 mL). Sodium hydroxide (1N) was added until the mixture became slightly cloudy. Methanol was again added (20 mL) until the solution was clear. Sodium hydroxide was again added until the mixture was slightly cloudy. The mixture was allowed to stir at room temperature overnight. The solution was concentrated to half its original volume and hydrochloric acid (2N) was added until the aqueous layer indicated a pH of about one. The mixture was extracted with dichloromethane and the organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated. The resulting material was chromatographed on silica gel using MeOH/heptane/dichloromethane (4/20/76) to give 3-acetyl-1-butyl-1H-indole-6-carboxylic acid (1.60 g). MS (ESI+) for Cl5H17N1O3+H1 m/z 260.13 (M+H)+.

後処理

  1. concentrationThe solution was concentrated to half its original volume and hydrochloric acid (2N)
  2. additionwas added until the aqueous layer
  3. extractionThe mixture was extracted with dichloromethane
  4. washthe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting material was chromatographed on silica gel

出典と根拠

ORDレコード
ord-18f7d1f395884a93b30eececd4c9866c
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

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