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

HRID 353470

반응식

HRID 353470 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매3회

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-879af4c043fb407ea9d2fc46a8361995
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06753342B2

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