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  (Organic Chemistry)

Alcohol to Ketone



Example 1

To a stirred solution of (COCl)2 (0.49 mL, 5.5 mmol) in DCM (12 mL) was slowly added DMSO (0.79 mL, 11.0 mmol) at -78 C. The resulting mixture was stirred at -78 C for 30 min. To the mixture was slowly added a solution of the SM (845 mg, 5.0 mmol) in DCM (10 mL) over 10 min, followed by the dropwise addition of TEA (3.1 mL, 22.5 mmol). The reaction mixture was slowly allowed to warm to RT. The mixture was stirred 1 h at RT, after which time it was quenched with H2O (10 mL). The mixture was extracted with DCM (3 x 20 mL). The combined organics were washed with 1M HCl (10 mL), sat aq Na2CO3, brine, dried (Na2SO4), and concentrated. The resulting material was purified by silica gel column chromatography (2:1 PE/EtOAc) to provide the product as an off-white solid. [600 mg, 72%]

[Patent Reference: WO2016011390, page 112, (20.2 MB)]