Triacetoxyperiodinane → HCID 67144165, compound

Temperature

-40 °C

The product from Step A (1.0 g, 3.5 mmol) and Dess-Martin periodinane (2.5 g) in dichloromethane (20 mL) were stirred overnight at room temperature and was then concentrated under reduced pressure. The residue was triturated with diethyl ether (50 mL) and filtered. The filtrate was washed with a solution of Na2S2O3.5H2O (12.5 g) in saturated aqueous sodium bicarbonate (100 mL), dried (MgSO4), filtered and evaporated. The residue was dissolved in anhydrous THF (50 mL). TiCl4 (3 mL) and methyl magnesium bromide in ethyl ether (3 M, 10 mL) were added at −78° C. and the mixture was stirred at −50 to −30° C. for 2 h. The mixture was poured into saturated aqueous sodium bicarbonate solution (100 mL) and filtered through Celite. The filtrate was extracted with toluene (100 mL) and evaporated. The residue was chromatographed on silica gel (EtOAc/hexane: 15/85) to afford the title compound as an oil (150 mg).

1. concentrationwas then concentrated under reduced pressure
2. customThe residue was triturated with diethyl ether (50 mL)
3. filtrationfiltered
4. washThe filtrate was washed with a solution of Na2S2O3.5H2O (12.5 g) in saturated aqueous sodium bicarbonate (100 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. customevaporated
8. dissolutionThe residue was dissolved in anhydrous THF (50 mL)
9. additionTiCl4 (3 mL) and methyl magnesium bromide in ethyl ether (3 M, 10 mL) were added at −78° C.
10. additionThe mixture was poured into saturated aqueous sodium bicarbonate solution (100 mL)
11. filtrationfiltered through Celite
12. extractionThe filtrate was extracted with toluene (100 mL)
13. customevaporated
14. customThe residue was chromatographed on silica gel (EtOAc/hexane: 15/85)

ORD record

ord-dfe8dc334d464e549a5d8ec994b6b755

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06777395B2