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

HRID 914842Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([C:10](OC)=[O:11])=[N:5][C:6]([CH3:9])=[CH:7][N:8]=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([CH:10]=[O:11])=[N:5][C:6]([CH3:9])=[CH:7][N:8]=1

Participants

Conditions

Temperature: -78 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-4c9e10d35ff541088600aebcc99421ee
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265108B2

Reaction notes

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