Methanol → 2-Methyl-2-(4-pyridin-3-yl-imidazol-1-yl)-propionaldehyde
Reaction equation
C([O:3][C:4](=O)[C:5]([CH3:18])([N:7]1[CH:11]=[C:10]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:9]=[CH:8]1)[CH3:6])C.[H-].C([Al+]CC(C)C)C(C)C.CO.C(OCC)(=O)C>C(Cl)Cl>[CH3:18][C:5]([N:7]1[CH:11]=[C:10]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[N:9]=[CH:8]1)([CH3:6])[CH:4]=[O:3]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 2-Methyl-2-(4-pyridin-3-yl-imidazol-1-yl)-propionic acid ethyl ester (1 eq) in DCM at −78° C. was added diisobutylaluminum hydride (4 eq). After leaving the reaction mixture stir at −78° C. for 3 hours, methanol (4 eq) was added to the reaction mixture at −78° C. and the solution was warmed to room temperature over 60 minutes. Ethyl acetate was added to the solution and after 30 minutes the solution was filtered and concentrated to give 2-Methyl-2-(4-pyridin-3-yl-imidazol-1-yl)-propionaldehyde (70%). MH++H2O (234).
Workup
- customAfter leaving the reaction mixture
- temperaturethe solution was warmed to room temperature over 60 minutes
- filtrationwas filtered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-84d0d3d3e0b44a649f55b6e0d911106b
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06756359B2
Reaction notes
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