Ethyl Acetate → HCID 86685848, compound

Temperature

0 °C

To a solution of Intermediate 2B (115 mmol) in anhydrous CH2Cl2 (320 mL) was added Dess-Martin periodinane (50.2 g, 118 mmol) portionwise at 0° C. The reaction was stirred at 0° C. for 0.5 h then at rt for 3 h. To the reaction was added 100 mL of sat'd aq Na2CO3 and 250 mL of EtOAc. The reaction was stirred for another 2 h. The insoluble material was removed by filtration. The layers were separated. The organic layer was washed with sat'd aq Na2CO3. Additional solids that formed upon standing overnight were removed. The organic solution was washed with sat'd aq NaCl, dried over anhydrous MgSO4, filtered and concentrated to provide a dark brown liquid, which was purified by silica gel chromatography (220 g silica gel, elute with EtOAc in hexanes to provide Intermediate 2C (26 g, 76%) as a colorless oil.

1. waitat rt for 3 h
2. stirringThe reaction was stirred for another 2 h
3. customThe insoluble material was removed by filtration
4. customThe layers were separated
5. washThe organic layer was washed with sat'd aq Na2CO3
6. customAdditional solids that formed
7. waitupon standing overnight
8. customwere removed
9. washThe organic solution was washed with sat'd aq NaCl
10. dry with materialdried over anhydrous MgSO4
11. filtrationfiltered
12. concentrationconcentrated
13. customto provide a dark brown liquid, which
14. customwas purified by silica gel chromatography (220 g silica gel
15. washelute with EtOAc in hexanes

ORD record

ord-fdaa27e430c14a5fad0e1a18a3d9d11c

Source dataset

uspto-grants-2014_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08791091B2