Tetrahydrofuran → (Quinolin-3-yl)methanol

To a solution of 4-quinolinecarboxaldehyde (0.47 g, 3.00 mmol) in a mixture of EtOH:THF=1:1 (40 mL) at 0° C. in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (0.11 g, 3.01 mmol) and the mixture was stirred overnight at RT. The solution was then cooled down to 0° C. before quenching a 6 N aq. HCl solution (2 mL). The reaction mixture was stirred at RT for 15 min then basified with a 2 N aq. NaOH solution (6 mL). EtOH was removed at 40° C. under vacuum and the residue was extracted with CH2Cl2 (2×50 mL). The organic phase was washed with brine (10 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum. Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 0:100) gave, after evaporation and drying, quinolin-4-ylmethanol MDE 32014 as an off-white solid (311 mg, 65% yield).

1. temperatureThe solution was then cooled down to 0° C.
2. custombefore quenching a 6 N aq. HCl solution (2 mL)
3. stirringThe reaction mixture was stirred at RT for 15 min
4. customEtOH was removed at 40° C. under vacuum
5. extractionthe residue was extracted with CH2Cl2 (2×50 mL)
6. washThe organic phase was washed with brine (10 mL)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated at 40° C. under vacuum
10. customPurification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 0:100)
11. customgave
12. customafter evaporation
13. customdrying

ORD record

ord-3b20608792974c8e8454e39f6d91af35

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772316B2