Water → 1-Ethyl-5-methyl-1H-imidazole-4-carbaldehyde

To a solution of 4-methyl-1H-imidazole-5-carbaldehyde (5.0 g, 45.4 mmol) in anhydrous THF (50 mL) was added diaza(1,3)bicyclo[5.4.0]undecane (DBU, 6.8 mL, 45.4 mmol) and iodoethane (3.4 mL, 45.4 mmol). The reaction mixture was stirred at room temperature overnight. Water (50 mL) was added before THF was evaporated. The mixture was extracted with EtOAc (1×50 mL) and 2-butanol (2×50 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-1% MeOH/DCM), affording 1-ethyl-5-methyl-1H-imidazole-4-carbaldehyde (730 mg, 12% yield).

1. customwas evaporated
2. extractionThe mixture was extracted with EtOAc (1×50 mL) and 2-butanol (2×50 mL)
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. customevaporated
6. customdried in vacuo
7. customThe crude product was purified by flash chromatography (0-1% MeOH/DCM)

ORD record

ord-90d43de008b04403b9ba14cf39fe6f74

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315521B2