Sodium borohydride → HCID 21069248, compound

Participants

Reaction Steps

The aldehyde from Example A6 (1.43 g, 3.81 mmol) in MeOH (15 mL) at 0° C. was treated with NaBH4 (144 mg, 3.81 mmol) in portions. Upon completion of addition, the ice bath was removed, and the mixture was stirred at room temperature for 2 hr. The reaction was then quenched with saturated NH4Cl (˜5 mL). After adding water (15 mL), the mixture was extracted with methylene chloride (3×30 mL). The organics were dried (magnesium sulfate). Concentration in vacuo afforded the alcohol as an oil (1.44 g, quantitative conversion). NMR(CDCl3) δ 1.28 (dt, 2H), 1.33–1.42 (m, 2H), 1.47–1.65 (m, 10H), 1.70 (d, 2H), 2.10 (dt, 2H), 2.32 (d, 2H), 2.94 (dt, 2H), 3.30 (dt, 2H), 3.68 (t, 2H), 3.76 (d, 2H), 3.96 (dd, 2H).

Provenance & Evidence