Ammonium Chloride → 1-[4-(tert-Butyldiphenylsilyloxymethyl)-1-(2-trimethylsilylethoxymethyl)-1H-imidazol-2-yl]ethanone

HRID 2273304

Reaktionsgleichung

Reaktionsgleichung von HRID 2273304
[Si:1]([O:18][CH2:19][C:20]1[N:21]=[CH:22][N:23]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.CON(C)[C:41](=[O:43])[CH3:42].[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C.CCCCCC>[Si:1]([O:18][CH2:19][C:20]1[N:21]=[C:22]([C:41](=[O:43])[CH3:42])[N:23]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH:24]=1)([C:14]([CH3:16])([CH3:17])[CH3:15])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Komponenten

8

Edukt 4

HCID 25517Ammonium ChlorideHCID 537505N-Methoxy-N-methylacetamideHCID 710872934-(tert-Butyldiphenylsilyloxymethyl)-1-(2-trimethylsilylethoxy methyl)-1H-imidazoleHCID 178418339Butyllithium

Produkt 1

HCID 710876851-[4-(tert-Butyldiphenylsilyloxymethyl)-1-(2-trimethylsilylethoxymethyl)-1H-imidazol-2-yl]ethanone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

The compound obtained in (1) (30.0 g) was dissolved in tetrahydrofuran (hereinafter sometimes referred to as THF) (500 mL) and cooled to −78° C. with stirring under an argon atmosphere. n-Butyllithium (a 2.66 M hexane solution, 36.2 mL) was slowly added dropwise to this solution by using a syringe, and stirring was conducted at the same temperature for 30 minutes. N-Methoxy-N-methylacetamide (13.1 mL) was then added by using a syringe, and stirring was continued for 90 minutes. A saturated aqueous solution of ammonium chloride was added to the reaction solution to stop the reaction, and extraction was conducted by using ethyl acetate. The combined extract liquid was washed with saturated brine and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by flash chromatography (ethyl acetate/hexane=5%→30%) using a silica gel column (trade name: Hi-Flash column 5L, manufactured by Yamazen Corporation) to give the title compound (24.4 g).

Aufarbeitung

  1. stirringstirring
  2. stirringstirring
  3. waitwas continued for 90 minutes
  4. customthe reaction, and extraction
  5. extractionThe combined extract liquid
  6. washwas washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resulting residue was purified by flash chromatography (ethyl acetate/hexane=5%→30%)

Quellen und Nachweise

ORD-Eintrag
ord-4bf47b36d1ff495c897b453d05a5eddf
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120835B2

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