Water → 5-(1,3-Dioxan-2-yl)-1-methyl-1H-imidazole

HRID 1942767

Reaktionsgleichung

Reaktionsgleichung von HRID 1942767
[CH3:1][N:2]1[C:6]([CH:7]=[O:8])=[CH:5][N:4]=[CH:3]1.[CH2:9](O)[CH2:10][CH2:11][OH:12].O>C1(C)C=CC=CC=1.C(Cl)Cl.CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O>[O:8]1[CH2:9][CH2:10][CH2:11][O:12][CH:7]1[C:6]1[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=1

Komponenten

7

Edukt 3

HCID 962WaterHCID 104421,3-PropanediolHCID 5735921-methyl-1H-imidazole-5-carbaldehyde

Produkt 1

HCID 579196325-(1,3-Dioxan-2-yl)-1-methyl-1H-imidazoleAusbeute 57,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-KatalysatorHCID 1140TolueneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1-methyl-1H-imidazole-5-carbaldehyde (2.9 g, 26.3 mmol) in toluene (20 mL) was added propane-1,3-diol (4.01 g, 52.7 mmol) and CSA (0.306 g, 1.317 mmol) and the reaction mixture was heated to reflux with azeotropic removal of the evolved water for 24 hours. The reaction mixture was cooled to RT, diluted with DCM and washed with NaHCO3 solution. It was then dried over Na2SO4, filtered and concentrated. Purification by column chromatography (80% EtOAc in Hexane to EtOAc) afforded 38 (2.53 g, 57% yield) as a yellow oil which solidified on standing to a yellow solid. MS (m/z): 169.2 (M+H).

Aufarbeitung

  1. temperaturethe reaction mixture was heated
  2. washwashed with NaHCO3 solution
  3. dry with materialIt was then dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography (80% EtOAc in Hexane to EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-8e30ab27481542f4b149006d25c476bc
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389541B2

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