Triacetoxyperiodinane → HCID 67142734, compound

Temperature

-30 °C

The product (2.0 g, 4.0 mmol) from Step B and Dess-Martin periodinane (2.0 g) in dichloromethane (30 mL) were stirred overnight at room temperature and was then concentrated under reduced pressure. The residue was triturated with ether ether (50 mL) and filtered. The filtrate was washed with a solution of Na2S2O3.5H2O (2.5 g) in saturated aqueous sodium bicarbonate solution (50 mL), dried (MgSO4), filtered and evaporated. The residue was dissolved in anhydrous Et2O (20 mL) and was added dropwise to a solution of MeMgBr in Et2O (3 M, 10 mL) at −78° C. The reaction mixture was allowed to warm to −30° C. and stirred at −30° C. to −15° C. for 5 h, then poured into saturated aqueous ammonium chloride (50 mL). The two layers were separated and the organic layer was dried (MgSO4), filtered and concentrated. The residue was chromatographed on silica gel (EtOAc/hexane: 1/9) to afford the title compound as a syrup (1.40 g).

1. concentrationwas then concentrated under reduced pressure
2. customThe residue was triturated with ether ether (50 mL)
3. filtrationfiltered
4. washThe filtrate was washed with a solution of Na2S2O3.5H2O (2.5 g) in saturated aqueous sodium bicarbonate solution (50 mL)
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. customevaporated
8. dissolutionThe residue was dissolved in anhydrous Et2O (20 mL)
9. additionwas added dropwise to a solution of MeMgBr in Et2O (3 M, 10 mL) at −78° C
10. additionpoured into saturated aqueous ammonium chloride (50 mL)
11. customThe two layers were separated
12. dry with materialthe organic layer was dried (MgSO4)
13. filtrationfiltered
14. concentrationconcentrated
15. customThe residue was chromatographed on silica gel (EtOAc/hexane: 1/9)

ORD record

ord-766c7590406546908c6e56076930589c

Source dataset

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06777395B2