EDTA disodium salt → trans-Stilbene oxide

Participants

Reaction Steps

To an acetonitrile solution (1.5 mL) of trans-stilbene (18 mg. 0.1 mmol) and ketone 4 (29.6 mg, 0.1 mmol) at room temperature was added an aqueous Na2EDTA solution (1 mL, 4×10-4M). To this homogenous solution was added in portions a mixture of sodium bicarbonate (1.55 mmol) and Oxone® (1 mmol). The reaction was finished in 7 min as shown by TLC. The reaction mixture was poured into water (20 mL), extracted with CH2Cl2 (3×20 mL) and dried with Na2SO4. After removal of the solvent under reduced pressure, the residue was purified by flash column chromatography; 20 g of silica gel (Merck, 230-400 mesh) in 100 mL of n-hexane with 2 mL of NEt3 was poured into a flash column of 20 mm diameter. The column was eluted with n-hexane (50 mL), followed by 5% EtOAc/n-hexane (150 mL) to give trans-stilbene epoxide (19.4 mg. 99% yield), and 40% EtOAc/n-hexane to give ketone 4 (27.6 mg. 93% yield of recovery).

Provenance & Evidence