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

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).

1. customThe layers were separated
2. washthe organic layer was washed with brine
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. dissolutionThe residue was redissolved in DCM (3 mL)
7. stirringThe reaction mixture was stirred at room temperature for 30 minutes
8. washwashed with 10% KOH
9. dry with materialThe organic layer was dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated
12. customThe crude product was purified on a silica gel column
13. washeluting with a gradient of 20-35% EtOAc/hexanes (with 1% TEA)

ORD record

ord-1f7fb00655b34de4ac2f4057a4ad16b8

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08742110B2