Sodium borohydride → HCID 68182277, compound

Participants

Reaction Steps

To a solution of 2-ethyl-6-methoxyquinoline-3-carbaldehyde SMA 44004 (256 mg, 1.19 mmol) in THF (12 mL) in a 25 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (48 mg, 1.25 mmol) and the mixture was stirred for 2 h at RT, then quenched by careful addition of 2 N aqueous HCl (2.6 mL). After stirring for 30 min at RT, the mixture was basified with 2 N aqueous NaOH (2.6 mL) and THF was removed at 40° C. under vacuum. The residue was diluted with CH2Cl2 (50 mL) and the organic phase was isolated, 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 50:50) gave (2-ethyl-6-methoxyquinolin-3-yl)-methanol SMA 44008 as a white solid (173 mg, 67% yield).

Provenance & Evidence