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Imidazole → 5-(4-{1-[4-(t-butyl-dimethyl-silanyloxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-4-methyl-thiophene-2-carboxylic Acid Methyl Ester

HRID 546839
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 546839
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[CH3:14][O:15][C:16]([C:18]1[S:19][C:20]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([CH2:41][CH3:42])([C:33]3[CH:38]=[CH:37][C:36]([OH:39])=[C:35]([CH3:40])[CH:34]=3)[CH2:31][CH3:32])=[CH:26][C:25]=2[CH3:43])=[C:21]([CH3:23])[CH:22]=1)=[O:17].C(OCC)C>CN(C)C=O>[CH3:14][O:15][C:16]([C:18]1[S:19][C:20]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([C:33]3[CH:38]=[CH:37][C:36]([O:39][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[C:35]([CH3:40])[CH:34]=3)([CH2:31][CH3:32])[CH2:41][CH3:42])=[CH:26][C:25]=2[CH3:43])=[C:21]([CH3:23])[CH:22]=1)=[O:17]
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Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 574434855-{4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl}-4-methyl-thiophene-2-carboxylic Acid Methyl Ester

Produkt 1

HCID 577090565-(4-{1-[4-(t-butyl-dimethyl-silanyloxy)-3-methyl-phenyl]-1-ethyl-propyl}-2-methyl-phenyl)-4-methyl-thiophene-2-carboxylic Acid Methyl Ester
Ausbeute 88.285 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

t-Butyldimethylsilyl chloride (36 mg, 0.238 mmol) and imidazole (40.5 mg, 0.595 mmol) were added to a solution of 5-{4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl}-4-methyl-thiophene-2-carboxylic acid methyl ester (Example 20-(1); 50.3 mg, 0.119 mmol) in N,N-dimethylformamide (0.2 mL) at room temperature, and the mixture was stirred at the same temperature for 0.2 hour. Diethyl ether was added to the reaction solution. The organic layer was washed with distilled water and brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=95/5 to ethyl acetate only) to give the title compound (56.4 g, 88.3%).

Aufarbeitung

  1. washThe organic layer was washed with distilled water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by silica gel chromatography (n-hexane/ethyl acetate=95/5 to ethyl acetate only)

Quellen und Nachweise

ORD-Eintrag
ord-93d05f1aad284ec09a338ebb73d32f55
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07935688B2

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