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Imidazole → Benzoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, methyl ester

HRID 1699739
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1699739
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[CH:5]=1.N1C=CN=C1.[Si:17](Cl)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18].[Cl-].[NH4+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH:5]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 88068Methyl 3-Hydroxybenzoate

Produkt 1

HCID 11715937Benzoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, methyl esterAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1.53 g of 3-hydroxybenzoic acid methyl ester and 1.69 g of imidazole were placed in a 50 ml flask, and a gas in the reaction system was replaced with nitrogen. 5 ml of DMF was added into the flask and stirred at 0° C. The obtained solution was mixed with 1.57 g of t-butyldimethylsilyl chloride, heated up to room temperature, simultaneously stirred overnight, and then mixed with a saturated aqueous solution of ammonium chloride to stop the reaction. The reaction solution was extracted with diethyl ether, and the obtained organic layer was sequentially washed with water, a saturated aqueous solution of potassium hydrogen sulfate and a saturated aqueous solution of sodium chloride and then dried over magnesium sulfate. The solvent was distilled away under reduced pressure to obtain 1.69 g of the title compound. Yield: 98%.

Aufarbeitung

  1. temperatureheated up to room temperature, simultaneously stirred overnight
  2. customthe reaction
  3. extractionThe reaction solution was extracted with diethyl ether
  4. washthe obtained organic layer was sequentially washed with water
  5. dry with materiala saturated aqueous solution of potassium hydrogen sulfate and a saturated aqueous solution of sodium chloride and then dried over magnesium sulfate
  6. distillationThe solvent was distilled away under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2e9693b4154849e39a7da7d17050cc96
Quelldatensatz
uspto-grants-2002_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06348478B1

Notizen zur Reaktion

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