Diisobutylaluminum hydride → 4,8-Diethoxy-2-methylquinoline-6-carbaldehyde

Participants

Reaction Steps

To a solution of ethyl 4,8-diethoxy-2-methylquinoline-6-carboxylate (60 mg, 0.20 mmol) in THF (2 mL) was added DIBAL (0.79 mL, 1M in toluene) at −78° C. The reaction mixture was allowed to warm up to room temperature and was stirred for 10 additional minutes before it was diluted with EtOAc (20 mL) and 5% KOH (20 mL). The layers were separated and the organic layer was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was redissolved in DCM (3 mL) and Dess-Martin periodinane (110 mg, 0.26 mmol) was added. The reaction mixture was stirred at room temperature for 30 minutes and was then diluted with EtOAc and washed with 10% KOH. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified on a silica gel column eluting with a gradient of 20-35% EtOAc/hexanes (with 1% TEA) to give the title intermediate (20 mg).

Provenance & Evidence