Sodium borohydride → (6-Methoxyquinolin-3-yl)methanol

To a stirred solution of 6-methoxyquinoline-3-carbaldehyde (1.00 g, 5.3 mmol) in THF (50 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (0.20 g, 5.3 mmol) and the mixture was stirred overnight at RT then cooled in an ice bath before quenching by addition of a 1 N aq. HCl solution (12 mL). After stirring for 15 min at RT, the mixture was basified to pH=9 with a 2 N aq. NaOH solution. THF was removed at 40° C. under vacuum and the solution was extracted with CH2Cl2 (200 mL), washed with brine (20 mL), dried over Na2SO4, filtered, and concentrated under vacuum. Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 0:100) gave (6-methoxyquinolin-3-yl)methanol SLA 47088A as a yellow solid (0.49 g, 49% yield).

1. temperaturethen cooled in an ice bath
2. custombefore quenching by addition of a 1 N aq. HCl solution (12 mL)
3. stirringAfter stirring for 15 min at RT
4. customTHF was removed at 40° C. under vacuum
5. extractionthe solution was extracted with CH2Cl2 (200 mL)
6. washwashed with brine (20 mL)
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under vacuum
10. customPurification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 0:100)

ORD record

ord-77b919bd3e704a9498fde23658395d54

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08772316B2