Sodium borohydride → 1-(3-Bromo-2-methylphenyl)-1-pentanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(3-bromo-2-methylphenyl)-1-pentanone (706 mg, 2.77 mmol) in anhydrous THF (12 mL) under nitrogen at 0° C. was added sodium borohydride (209 mg, 5.53 mmol) in water (8 mL) and the resulting mixture stirred at 0° C. for 2 h. Additional sodium borohydride (105 mg, 2.77 mmol) was then added, along with more THF (40 mL), and the resulting mixture stirred at 0° C. for an additional 30 min. The reaction mixture was then partitioned between EtOAc (50 mL) and water (50 mL), the layers separated, and the aqueous re-extracted with EtOAc (50 mL). The combined organic solution was then dried (Na2SO4) filtered, and reduced under vacuum. Purification by SPE (silica, 20 g cartridge), eluted with cyclohexane:EtOAc (gradient 99:1 to 19:1) afforded the title compound as a colourless oil (495 mg).

Provenance & Evidence