Hydrochloric Acid → 3-Methoxy-6-methylpyrazine-2-carbaldehyde

Temperature

-78 °C

After dissolving 300 mg of methyl 3-methoxy-6-methylpyrazine-2-carboxylate in a mixture of 5 ml toluene/5 ml dichloromethane, the solution was cooled to −78° C. Next, 1.21 ml of diisobutylaluminium hydride (1.5 M, toluene solution) was added dropwise and the mixture was stirred for 1 hour. After adding 10 ml of 1N hydrochloric acid dropwise to the reaction solution, extraction was performed with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, a saturated sodium bicarbonate solution and saturated brine in that order and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (118 mg, 47% yield).

1. extractiondropwise to the reaction solution, extraction
2. washThe organic layer was washed with 1N hydrochloric acid
3. dry with materiala saturated sodium bicarbonate solution and saturated brine in that order and dried over anhydrous magnesium sulfate
4. distillationthe solvent was distilled off under reduced pressure
5. customThe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)

ORD record

ord-f6aa40e154044ee8b232064ab08df070

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07915274B2