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-cbea47a7dae1471881af0240a89aad64

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040538B2