Tetrahydrofuran → 4-(1-Hydroxyethyl)-1-(dimethylethoxycarbonyl)imidazole
Reaction equation
[CH3:1][C:2]([CH3:14])([O:4][C:5]([N:7]1[CH:11]=[C:10]([CH:12]=[O:13])[N:9]=[CH:8]1)=[O:6])[CH3:3].O1CCC[CH2:16]1>>[OH:13][CH:12]([C:10]1[N:9]=[CH:8][N:7]([C:5]([O:4][C:2]([CH3:14])([CH3:1])[CH3:3])=[O:6])[CH:11]=1)[CH3:16]Participants
3
Procedure
To a solution of 1-(dimethylethoxycarbonyl)imidazole-4-carboxaldehyde (9.3 g, 47 mmol) in tetrahydrofuran (200 mL) was added a methyl Grignard reagent (6.6 mL, 50 mmol) at ambient temperature. The resulting reaction mixture was stirred overnight at ambient temperature. The reaction was quenched with water and extracted with ethyl acetate. The organic layer was dried (Na2SO4) and concentrated to afford 10 g of 4-(1-hydroxyethyl)-1-(dimethylethoxycarbonyl)imidazole as an oil.
Workup
- customThe resulting reaction mixture
- customThe reaction was quenched with water
- extractionextracted with ethyl acetate