Hydrochloric Acid → HCID 118222766, compound

Temperature

-20 °C

To a solution of diisopropylamine (0.13 mL, 0.918 mmol) in 2 mL anhydrous tetrahydrofuran at −40° C. was added n-butyllithium (0.34 mL, 2.5 M in hexanes) dropwise. The solution was stirred while warming to −20° C. over 20 minutes. After cooling to −78° C., 4-butyl-1-methyl-1H-imidazole (95 mg, 0.765 mmol) was added dropwise as a solution in 2 mL anhydrous tetrahydrofuran. The resulting solution was stirred for 40 minutes at −78° C. Dimethylformamide (0.24 mL, 3.06 mmol) was added and the solution stirred while warming to room temperature. The reaction mixture was poured into 15 mL of 1 N hydrochloric acid and stirred for 5 minutes. The pH of the reaction mixture was adjusted to 7-8 by careful addition of saturated sodium bicarbonate solution. Organics were extracted with dichloromethane (3×20 mL), dried over magnesium sulfate, filtered and concentrated. The crude residue was subjected to chromatography on silica gel with gradient elution (5-50% ethyl acetate in hexanes) to give 1-methyl-4-propyl-1H-imidazole-2-carbaldehyde (9 mg, 8%) as an off-white solid. Used without further characterization.

1. temperatureAfter cooling to −78° C.
2. stirringThe resulting solution was stirred for 40 minutes at −78° C
3. stirringthe solution stirred
4. temperaturewhile warming to room temperature
5. stirringstirred for 5 minutes
6. extractionOrganics were extracted with dichloromethane (3×20 mL)
7. dry with materialdried over magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. washThe crude residue was subjected to chromatography on silica gel with gradient elution (5-50% ethyl acetate in hexanes)

ORD record

ord-aba91b8be27048d295b4aa479ed3c21d

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315495B2