Alcohol to Aldehyde

(Dess-Martin Periodinane)

Examples:

Example 1

Dess-Martin Oxidation

To a solution of the SM (740 mg, 5.2 mmol) in DCM (18 mL) at 0 C was added Dess-Martin periodinane (4.6 g, 10.9 mmol). The reaction mixture was stirred at RT for 3 h. The mixture was quenched with Na2S2O3 and NaHCO3, and extracted with EtOAc (2 x 50 mL). The combined organics were washed with brine (2 x 20 mL), dried (Na2SO4), and concentrated. The resulting material was purified by silica gel column chromatography (10% EtOAc/hexane) to provide the product as a yellow solid. [275 mg, 38%]

[Patent Reference: WO2015129926, page 79, (21.5 MB)]

Example 2

To a solution of the SM (11.4 g, 27.6 mmol) in DCM (150 mL) at 0 C was added Dess-Martin periodinane (14.1 g, 33.2 mmol). The reaction mixture was stirred at 0 C for 30 min, then RT for an additional 60 min. The mixture was neutralized with aq NaHCO3 and diluted with EtOAc. The mixture was washed with H2O, brine, concentrated, and purified by silica gel flash chromatography to provide the product. [10.5 g, 93%]

[Patent Reference: WO2016014463, page 63, (6.7 MB)]

Example 3

To a solution of the SM (4.5 g, 29.6 mmol) in DCM (80 mL) was added Dess-Martin periodinane (51.1 g, 35.5 mmol) at 0 C. The reaction mixture was stirred at 0 C for 1 h. The mixture was diluted with DCM (100 mL), washed with sat aq NaHCO3 (2 x 100 mL), brine, dried (Na2SO4), and concentrated. The crude residue was purified by silica gel chromatography (10-50% EtOAc/hexane) to provide the product as a yellow oil. [2.5 g, 56%]

[Patent Reference: WO2015140133, page 108, (11.7 MB)]