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

HRID 1942767

Reaction equation

HRID 1942767 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].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

Participants

7

Reactant 3

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

Product 1

HCID 579196325-(1,3-Dioxan-2-yl)-1-methyl-1H-imidazoleYield 57.2%

Reagents, catalysts & solvents 3

HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-CatalystHCID 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. 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).

Workup

  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)

Sources & evidence

ORD record
ord-8e30ab27481542f4b149006d25c476bc
Source dataset
uspto-grants-2013_03
Patent number
US08389541B2

Linked notes

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