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

HRID 84358

Reaction equation

HRID 84358 reaction equation
[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].CC1(C)C2(CS(O)(=O)=O)C(CC1CC2)=O.O>C1(C)C=CC=CC=1.C(Cl)Cl>[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

Participants

7

Reactant 4

HCID 962WaterHCID 104421,3-PropanediolHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 5735921-methyl-1H-imidazole-5-carbaldehyde

Product 1

HCID 579196325-(1,3-Dioxan-2-yl)-1-methyl-1H-imidazole

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. temperaturethe reaction mixture was heated
  2. washwashed with NaHCO3 solution

Sources & evidence

ORD record
ord-e7428bd3e70b498dbb8013ec465cb6e1
Source dataset
uspto-grants-2014_09
Patent number
US08846927B2

Linked notes

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