Toluene → 5-benzyloxy-6-isopropyl-1,3-dimethyl-1H-indole

HRID 38342

反応式

HRID 38342 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[CH:18]([CH3:20])[CH3:19])[NH:14][CH:13]=[C:12]2[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].CI.[C:26]1(C)C=CC=CC=1>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[CH:18]([CH3:19])[CH3:20])[N:14]([CH3:26])[CH:13]=[C:12]2[CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

7

反応物 4

HCID 1140TolueneHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 595986035-benzyloxy-6-isopropyl-3-methyl-1H-indole

生成物 1

HCID 595987425-benzyloxy-6-isopropyl-1,3-dimethyl-1H-indole

試薬・触媒・溶媒 2

HCID 159952Benzyltributylammonium chloride触媒HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

5-Benzyloxy-6-isopropyl-3-methyl-1H-indole (0.320 g, 1.15 mmol), KOH (0.264 g, 4.7 mmol), benzyl tributylammonium chloride (0.071 g, 0.230 mmol), and methyl iodide (0.107 mL, 1.72 mmol) were added to 3 mL of toluene. The resulting mixture was stirred for 4 hours at 90° C., cooled to room temperature, poured into water, and extracted with ethyl acetate 2 times. The combined organic layers were washed with water, dried (MgSO4), and evaporated in vacuo to provide a crude oil that was purified with flash chromatography (ethyl acetate/hexanes=1/9); yield 270 mg of 5-benzyloxy-6-isopropyl-1,3-dimethyl-1H-indole.

後処理

  1. temperaturecooled to room temperature
  2. extractionextracted with ethyl acetate 2 times
  3. washThe combined organic layers were washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customto provide a crude oil that
  7. customwas purified with flash chromatography (ethyl acetate/hexanes=1/9)

出典と根拠

ORDレコード
ord-a73ad4848b2a485e8a88867322cf28f5
出典データセット
uspto-grants-2013_09
特許番号
US08524725B2

関連ノート

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