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  (Summer Internship)


  (Organic Chemistry)

Alkene to Alcohol

(Ozone + NaBH4)


Example 1

A solution of the SM (3.00 g, 8.26 mmol) in DCM (60 mL) was cooled to -78 C. Ozone was bubbled through the solution for 10 min. The excess ozone was removed via N2 purge. NaBH4 (1.25 g, 33.0 mmol) and EtOH (20 mL) was added. The reaction mixture was warmed to RT and stirred for 4 h, after which time H2O and DCM were added. The layers were separated and the org layer was washed with brine, dried (MgSO4), and concentrated. The resulting material (3.2 g) was purified by Prep LC (120 g silica, 0-40% EtOAc/heptane) to provide the product as a colorless oil. [1.07 g, 35%]

[Patent Reference: WO2015144799, page 310, (18.8 MB)]