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Chloromethyl Methyl Ether → 2-(4-t-Butylphenyl)-3-methoxymethyloxy-4-ethoxycarbonylthiophene

HRID 1881528
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1881528
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[S:14][CH:15]=[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:17]=2[OH:18])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].[CH3:24][O:25][CH2:26]Cl.[Cl-].[NH4+]>CN(C)C=O>[C:3]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[S:14][CH:15]=[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:17]=2[O:18][CH2:24][O:25][CH3:26])=[CH:11][CH:12]=1)([CH3:6])([CH3:4])[CH3:5]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 670503332-(4-t-Butylphenyl)-3-hydroxy-4-ethoxycarbonylthiophene

Produkt 1

HCID 670503162-(4-t-Butylphenyl)-3-methoxymethyloxy-4-ethoxycarbonylthiopheneAusbeute 92,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

60% Sodium hydride (28 mg, 0.69 mmol) was added to a solution of 2-(4-t-butylphenyl)-3-hydroxy-4-ethoxycarbonylthiophene (0.20 g, 0.66 mmol) obtained in accordance with JP-A-48-26755 in dimethylformamide (1.0 mL) at room temperature, and the reaction solution was stirred at 60° C. for 15 minutes. After the reaction solution was cooled to room temperature, chloromethyl methyl ether (0.055 mL, 0.73 mmol) was added dropwise, and the reaction solution was stirred at room temperature for another 5 hours. After addition of saturated aqueous ammonium chloride, the reaction solution was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate. The organic layer was concentrated and purified by silica gel column chromatography (chloroform) to give the desired product as a colorless oil (212 mg, yield 91%).

Aufarbeitung

  1. temperatureAfter the reaction solution was cooled to room temperature
  2. stirringthe reaction solution was stirred at room temperature for another 5 hours
  3. extractionthe reaction solution was extracted with ethyl acetate
  4. washthe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe organic layer was concentrated
  7. custompurified by silica gel column chromatography (chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-ed33035b8f344928a5a74ac07ea6225b
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08318796B2

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