Dimethylformamide → 1-Methyl-4-phenyl-1H-imidazole-2-carboxaldehyde

Temperature

-40 °C

To a solution of 1-methyl-4-phenyl-1H-imidazole 42 (0.512 g, 3.24 mmol) in THF (15 mL) at −40° C. was added n-butyllithium (2.40 mL, 3.84 mmol) (1.6 M in hexanes), stirred at −40° C. for 30 min, cooled to −78° C., and N,N-dimethylformamide (0.325 mL, 4.21 mmol) was added. The reaction mixture was warmed to room temperature over 1 h, stirred at room temperature for 2 h, diluted with EtOAc, washed with water (1×), brine (1×), dried over MgSO4, filtered, and concentrated. The crude product was dissolved in DCM (˜20 mL), diluted with hexanes (˜50 mL), and concentrated to a volume of approximately 30 mL. The solution was cooled to 0° C. and the solid was collected by filtration, washed with hexanes, and dried under high vacuum to give 1-methyl-4-phenyl-1H-imidazole-2-carbaldehyde 43. Mass spectrum: calculated for C11H10N2O 186.1; found 187.1 (M++1).

1. temperaturecooled to −78° C.
2. temperatureThe reaction mixture was warmed to room temperature over 1 h
3. stirringstirred at room temperature for 2 h
4. washwashed with water (1×), brine (1×)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. dissolutionThe crude product was dissolved in DCM (˜20 mL)
9. additiondiluted with hexanes (˜50 mL)
10. concentrationconcentrated to a volume of approximately 30 mL
11. temperatureThe solution was cooled to 0° C.
12. filtrationthe solid was collected by filtration
13. washwashed with hexanes
14. customdried under high vacuum

ORD record

ord-2a1128d263eb48a7908b81e908c33937

Source dataset

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08334317B2