Triacetoxyperiodinane → HCID 72546824, compound

Temperature

0 °C

An oven-dried 25 mL one-necked round-bottomed flask equipped with a septum and a stir bar was charged with Dess-Martin periodinane (DMP, 0.063 g, 0.15 mmol) in dry CH2Cl2 (5 mL). The solution was cooled to 0° C. in an ice bath for 10 min, compound 15b (0.045 g, 0.14 mmol) in dry CH2Cl2 (5 mL) was added and the mixture mas stirred at 0° C. for 5 min. The reaction was then warmed to rt and stirred for an additional 15 min. The consumption of the starting material was monitored by TLC (AcOEt/n-hexane 4:6). The reaction was then quenched with sat'd aq NaHCO3 solution (20 mL). The aqueous layer was extracted with Et2O (3×20 mL). The combined organic layers were washed with brine (30 mL), dried over MgSO4, gravity filtered, and concentrated under reduced pressure. The crude product was purified by silica gel flash column chromatography, eluting with AcOEt/n-hexane 3:7, to provide 0.031 g of the title compound as an orange solid in a 67% yield.

1. customAn oven-dried 25 mL one-necked round-bottomed flask equipped with a septum and a stir bar
2. temperatureThe reaction was then warmed to rt
3. stirringstirred for an additional 15 min
4. customThe consumption of the starting material
5. customThe reaction was then quenched with sat'd aq NaHCO3 solution (20 mL)
6. extractionThe aqueous layer was extracted with Et2O (3×20 mL)
7. washThe combined organic layers were washed with brine (30 mL)
8. dry with materialdried over MgSO4, gravity
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe crude product was purified by silica gel flash column chromatography
12. washeluting with AcOEt/n-hexane 3:7

ORD record

ord-55ad2b665d044b718a0e46499f61b2fe

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133234B2