Alkene to Alcohol

(Hydroboration-Oxidation)

Examples:

Example 1

To a solution of the SM (500 mg, 1.82 mmol) in THF (5 mL) was added 9-BBN (0.5 M in THF, 7.30 mL, 3.65 mmol) at RT. The mixture was stirred at RT for 2 h, until no SM was detected by TLC. To the mixture at 0 C was added aq 3.0 M NaOH (0.91 mL, 2.73 mmol), followed by H2O2 (30% in H2O, 1.1 mL, 9.1 mmol). The reaction mixture was stirred at RT for 1 h, after which time it was diluted with brine (20 mL) and extracted with EtOAc (3 x 30 mL). The combined organics were dried (Na2SO4), concentrated, and purified by a flash chromatography column (1:20 to 1:3 EtOAc/PE) to provide the product as a colorless oil. [400 mg, 75%]

[Patent Reference: WO2016011930, page 141, (15.7 MB)]