Water → 2-(3{[tert-Butyl(dimethyl)silyl]oxy}propyl)-1H-benzimidazole

HRID 1610796

Reaktionsgleichung

Reaktionsgleichung von HRID 1610796
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH:9][CH2:10][CH2:11][CH2:12][C:13]1[NH:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1.C(N(CC)CC)C.O>CN(C=O)C>[Si:1]([O:9][CH2:10][CH2:11][CH2:12][C:13]1[NH:14][C:15]2[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=2[N:17]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 754702-Benzimidazolepropanol

Produkt 1

HCID 695919622-(3{[tert-Butyl(dimethyl)silyl]oxy}propyl)-1H-benzimidazoleAusbeute 97,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To this end, tert-butyldimethylsilyl chloride (TBDMSCI) (14.68 g, 97.37 mmol) was added a little at a time to a solution of 2-(3-hydroxypropyl)-benzimidazole (15.60 g, 88.52 mmol) in DMF (265 ml) and triethylamine (20.27 ml, 145.41 mmol). The mixture was stirred at RT overnight and then admixed with water (800 ml) and extracted with diethyl ether. The organic phase was dried over sodium sulphate and chromatographed over silica gel (mobile phase: cyclohexane/ethyl acetate=6:1), giving 25 g (97%) of colourless crystals. MS (DCI): 291 (M+H)+

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customchromatographed over silica gel (mobile phase: cyclohexane/ethyl acetate=6:1)

Quellen und Nachweise

ORD-Eintrag
ord-fcb477d18a744f849491a493dcf7f30a
Quelldatensatz
uspto-grants-2006_01
Patentnummer
US06984642B1

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