Sodium borohydride → HCID 68182175, compound

Participants

Reaction Steps

To a stirred solution of 5-ethoxyquinoline-3-carbaldehyde CCH 29158B (98 mg, 487 μmol) in THF (10 mL) at 0° C. in a 50 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (18 mg, 476 μmol) and the mixture was stirred overnight at RT then cooled in an ice bath before quenching by addition of a 6 N aq. HCl solution (0.33 mL). After stirring for 15 min at that temperature, the mixture was basified by a 2 N aq. NaOH solution (1.0 mL). THF was then removed at 40° C. under vacuum and the solution was extracted with CH2Cl2 (50 mL), washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated under vacuum. Purification by column chromatography (SiO2, eluent CH2Cl2:MeOH=100:0 to 97:3) provided 41 mg (5-ethoxyquinolin-3-yl)methanol MDE 32076 as a colorless oil (41 mg, 41% yield).

Provenance & Evidence