4-(4-Methoxy-phenyl)-2-methyl-thiazole → 2-[7-(Tert-butyldimethylsilanyloxy)heptyl]-4-(4-methoxyphenyl)thiazole

HRID 1039148

Reaktionsgleichung

Reaktionsgleichung von HRID 1039148
C([Li])(C)(C)C.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16]([CH3:19])[S:17][CH:18]=2)=[CH:10][CH:9]=1.Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>O1CCCC1.[NH4+].[Cl-].[Cl-].[Na+].O>[Si:28]([O:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:19][C:16]1[S:17][CH:18]=[C:14]([C:11]2[CH:12]=[CH:13][C:8]([O:7][CH3:6])=[CH:9][CH:10]=2)[N:15]=1)([C:31]([CH3:32])([CH3:33])[CH3:34])([CH3:30])[CH3:29]

Komponenten

7

Edukt 3

HCID 7687654-(4-Methoxy-phenyl)-2-methyl-thiazoleHCID 4260352(6-Bromohexyloxy)-tert-butyldimethylsilaneHCID 178418306HCID 178418306, Verbindung

Produkt 1

HCID 684899302-[7-(Tert-butyldimethylsilanyloxy)heptyl]-4-(4-methoxyphenyl)thiazoleAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittelHCID 25517Ammonium ChlorideLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Add a solution of tert-butyllithium (26.35 mmol, 15.5 mL, 1.7 M in hexanes) dropwise to a solution of 4-(4-methoxyphenyl)-2-methylthiazole (6.15 g, 29.9 mmol) in degassed anhydrous tetrahydrofuran (THF) (100 mL) at −78° C. under nitrogen and stir the solution for 45 minutes. To this solution, add a solution of (6-bromohexyloxy)-tert-butyldimethylsilane (7.20 g, 24.4 mmol) over 5 min and stir the mixture for 2 hours. Warm the mixture to 0° C., dilute with NH4Cl (200 mL) and brine (250 mL) and extract with methylene chloride (3×150 mL). Dry the combined organic extracts over magnesium sulfate and remove the solvent under reduced pressure. Purify the crude product by flash column chromatography on silica gel, eluting with hexanes/ethyl acetate (5:1), to provide 2-[7-(tert-butyldimethylsilanyloxy)heptyl]-4-(4-methoxyphenyl)thiazole (6.27 g, 50%).

Aufarbeitung

  1. stirringstir the mixture for 2 hours
  2. extractionextract with methylene chloride (3×150 mL)
  3. dry with materialDry the combined organic extracts over magnesium sulfate
  4. customremove the solvent under reduced pressure
  5. customPurify the crude product by flash column chromatography on silica gel
  6. washeluting with hexanes/ethyl acetate (5:1)

Quellen und Nachweise

ORD-Eintrag
ord-43b4714b1e834389a98d280abefa4705
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08552039B2

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