Indole → 1-[(2,4,6-Trimethylphenyl)methyl]-1H-indole

HRID 353470

反応式

HRID 353470 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH3:12][C:13]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:14]=1[CH2:15]Cl.O>CS(C)=O>[CH3:12][C:13]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:14]=1[CH2:15][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

参加物

6

反応物 4

HCID 798IndoleHCID 962WaterHCID 24758Sodium hydrideHCID 741082,4,6-Trimethylbenzyl chloride

生成物 1

HCID 222567421-[(2,4,6-Trimethylphenyl)methyl]-1H-indole収率 87.2%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒3 回

反応条件

温度
60 °C

実験手順

A solution of indole (1.185 g) in dry DMSO (3 ml) is dropped into a suspension of sodium hydride (60% mineral oil suspension; 0.44 g) in dry DMSO (10 ml). After two hours, the resulting solution is added with a solution of 2,4,6-trimethylbenzyl chloride (1.9 g) in dry DMSO (2 ml) heating at 60° C. for 6 h. The reaction mixture is kept at room temperature overnight, then poured into water (250 ml) extracted with ethyl acetate and dried (Na2SO4). The drying agent is filtered off, the solvent is evaporated off under reduced pressure and the resulting residue is purified by column chromatography (silica gel; eluent n-hexane/AcOEt 9/1) to obtain 2.2 g of 1-(2,4,6-trimethylbenzyl)indole.

後処理

  1. waitThe reaction mixture is kept at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (Na2SO4)
  4. filtrationThe drying agent is filtered off
  5. customthe solvent is evaporated off under reduced pressure
  6. customthe resulting residue is purified by column chromatography (silica gel; eluent n-hexane/AcOEt 9/1)

出典と根拠

ORDレコード
ord-879af4c043fb407ea9d2fc46a8361995
出典データセット
uspto-grants-2004_06
特許番号
US06753342B2

関連ノート

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