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Imidazole → 2-[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)benzyl]-1H-isoindole-1,3(2H)-dione

HRID 585516
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HRID 585516 반응식
N1C=CN=C1.[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[OH:14][CH2:15][C:16]1[CH:17]=[C:18]([CH:31]=[CH:32][CH:33]=1)[CH2:19][N:20]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]1=[O:30].O>O1CCCC1.ClCCl>[Si:6]([O:14][CH2:15][C:16]1[CH:17]=[C:18]([CH:31]=[CH:32][CH:33]=1)[CH2:19][N:20]1[C:21](=[O:30])[C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:28]1=[O:29])([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 223370702-[3-(hydroxymethyl)benzyl]-1H-isoindole-1,3(2H)-dione

생성물 1

HCID 208241182-[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)benzyl]-1H-isoindole-1,3(2H)-dione

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
HCID 8028Tetrahydrofuran용매

실험 절차

Under argon and at room temperature, imidazole (1.0 g, 15.0 mmol) and tert-butyldimethylsilyl chloride (1.7 g, 11.2 mmol) are added to a solution of 2-[3-(hydroxymethyl)benzyl]-1H-isoindole-1,3(2H)-dione (2.0 g, 7.5 mmol) in tetrahydrofuran (22.5 ml). The reaction mixture is stirred at room temperature for 16 h, and water is added. After addition of dichloromethane and phase separation, the aqueous phase is extracted with dichloromethane. The combined organic phases are dried (sodium sulfate), filtered and concentrated under reduced pressure. The desired product is purified by flash chromatography (petroleum ether/ethyl acetate mixtures). Yield: 2.7 g, 95% of theory.

후처리

  1. extractionthe aqueous phase is extracted with dichloromethane
  2. dry with materialThe combined organic phases are dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe desired product is purified by flash chromatography (petroleum ether/ethyl acetate mixtures)

출처 및 근거

ORD 기록
ord-603173c4e4244fa4b1c5d56e1ed83366
출처 데이터셋
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06933295B2

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