Methanol → HCID 67423695, compound

Jones reagent (2 ml) was added dropwise to a stirred solution of the tetrol 7 (0.19 g, 0.45 mmol) in acetone (25 ml) at 0° C. and the mixture was stirred at room temperature for 1 h. Methanol (8 ml) was then added and the oxidized product was extracted with EtOAc (2×50 ml). The combined organic layers were dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The residue was dissolved in MeOH (80 ml), pTSA was added and the mixture was stirred at room temperature for 2 h. The solvent was evaporated under reduce pressure, the residue was dissolved in CHCl3 (50 ml), washed with a saturated aqueous solution of sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml). The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography using from 20 to 30% EtOAc in petroleum ether to afford the methyl ester 8 (0.115 g, 0.26 mmo, 58%1) as whitish solid.

1. extractionthe oxidized product was extracted with EtOAc (2×50 ml)
2. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
3. customevaporated to dryness under reduced pressure
4. dissolutionThe residue was dissolved in MeOH (80 ml)
5. additionpTSA was added
6. stirringthe mixture was stirred at room temperature for 2 h
7. customThe solvent was evaporated
8. dissolutionthe residue was dissolved in CHCl3 (50 ml)
9. washwashed with a saturated aqueous solution of sodium bicarbonate (2×50 ml), water (50 ml) and brine (50 ml)
10. dry with materialThe organic layer was dried over anhydrous sodium sulfate
11. customevaporated to dryness
12. customThe residue was purified by flash chromatography

ORD record

ord-fb828c0c672e45be9e316dba1aae6ffd

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08999964B2