Diisobutylaluminum hydride → Quinoxaline-6-carboxaldehyde

HRID 1771125Notes

Reaction equation

CON(C)[C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[N:9]2)=[O:5].CC(C[AlH]CC(C)C)C>C1COCC1>[N:12]1[C:13]2[C:8](=[CH:7][C:6]([CH:4]=[O:5])=[CH:15][CH:14]=2)[N:9]=[CH:10][CH:11]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of N-methoxy-N-methylquinoxaline-6-carboxamide (4.34 g, 20 mmol, 1.0 eq.) in THF (40 mL) cooled at −78° C. was added DiBAl—H (40 mL, 40 mmol, 2.0 eq.) dropwise. The resulted mixture was stirred at −78° C. for 30 min, then quenched by the addition of aqueous NH4Cl solution. The mixture was adjusted to pH 7 with HCl (1N, 60 mL) and extracted with EA (50 mL×3). The organic layers were combined, dried over anhydrous Na2SO4 and concentrated. The resulting residue was purified via flash column chromatography (PE/EA=4/1, v/v) to afford quinoxaline-6-carbaldehyde as yellow solid (2.96 g, 93.7%).

Workup

customquenched by the addition of aqueous NH4Cl solution
extractionextracted with EA (50 mL×3)
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated
customThe resulting residue was purified via flash column chromatography (PE/EA=4/1, v/v)

Sources & evidence

ORD record: ord-0eb4cdbe9cf94fb78cfd1a3e48d1b435
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249110B2

Reaction notes

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