EDTA disodium salt → 1,1-Dioxo-tetrahydro-thiopyran-4-one

To a solution of tetrahydrothiopyran-4-one (400 mg, 3.45 mmol) in acetonitrile (5 ml) was added aqueous Na2EDTA (3 ml, 0.0004 M). A mixture of oxone (6.30 g, 10.30 mmol) and sodium bicarbonate (2.70, 32 mmol) was added in small portions to the above solution over a period of 20 min. The slurry was stirred for another 1 h before being quenched with methylene chloride. The organic solvent was decanted and the solid residue was triturated with ethyl acetate (3×25 ml). The combined organic layers were dried over sodium sulfate and concentrated to give the desired ketone (0.37 g, 73%) as a colorless solid. mp 170-172° C. (lit. 168-170° C.); 1H NMR (500 MHz, CDCl3) 2.99 (t, J=6.8 Hz, 4H), 3.39 (t, J=6.8 Hz, 4H). Ref: Yang, D.; Yip, Y.-C.; Jiao, G.-S.; Wong, M.-K. Design of Efficient Ketone Catalysts for Epoxidation by Using the Field Effect. J. Org. Chem, 1998, 63, 8952-8956.

1. additionwas added in small portions to the above solution over a period of 20 min
2. custombefore being quenched with methylene chloride
3. customThe organic solvent was decanted
4. customthe solid residue was triturated with ethyl acetate (3×25 ml)
5. dry with materialThe combined organic layers were dried over sodium sulfate
6. concentrationconcentrated

ORD record

ord-532bfc4de74842bba2acf6d8b317ba25

Source dataset

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06906205B2