EDTA disodium salt → (R,R)-Stilbene oxide

Temperature

0 °C

Aqueous Na2EDTA (1×10−4 M, 10 mL) and a catalytic amount of tetrabutylammonium hydrogen sulfate were added to a solution of trans-stilbene (0.18 g, 1 mmol) in acetonitrile (15 mL) with vigorous stirring at 0° C. A mixture of Oxone® (3.07 g, 5 mmol) and sodium bicarbonate (1.3 g, 15.5 mmol) was pulverized and a small portion of this mixture was added to the reaction mixture to bring the pH to >7. After 5 min, ketone 1 (0.77 g, 3 mmol) was added portionwise over a period of 1 h. Simultaneously, the rest of Oxone® and sodium bicarbonate was added portion was added portionwise over 50 min. After the completion of the addition of ketone 1, the reaction mixture was stirred for another 1 h at 0° C., diluted with water (30 mL), and extracted with hexanes (4×40 mL). The combined extracts were washed with brine, dried (Na2SO4), filtered, concentrated, and purified by flash chromatography [the silica gel was buffered with 1% triethylamine solution in hexane; hexane/ether (1/0 to 50/1, V/V) was used as the eluent] to afford trans-stilbene oxide as white crystals (0. 149 g, 73% yield, 95.2% ee).

1. additiona small portion of this mixture was added to the reaction mixture
2. additionwas added portionwise over 50 min
3. stirringthe reaction mixture was stirred for another 1 h at 0° C.
4. extractionextracted with hexanes (4×40 mL)
5. washThe combined extracts were washed with brine
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated
9. custompurified by flash chromatography [the silica gel

ORD record

ord-5dd64fa583ce4e688abb27d199c2fd45

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06686483B2