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

HRID 585516
ノート
印刷プレビュー

反応式

HRID 585516 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344
Dichloromethane
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-603173c4e4244fa4b1c5d56e1ed83366
出典データセット
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06933295B2

反応ノート

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