Hydrogen Peroxide → (1R,2S)-2-(3-pyridyl)tetrahydro-2H-thiopyran 1-oxide

A solution of (S)-2-(3-pyridyl)tetrahydro-2H-thiopyran (1.5 g) in dichloromethane (15 ml) is treated with ethanol (15 ml), followed by copper acetylacetonate (0.22 g). The green-blue solution is treated with a solution of hydrogen peroxide (2 ml; 27.5%) in ethanol (2 ml). After 2 hours the solution is treated with a further quantity of solution of hydrogen peroxide (1 ml; 27.5%) in ethanol (1 ml), followed by a similar further quantity each hour for seven hours. Thus, a total of 10 ml of 27.5% hydrogen peroxide is used. After a further period of four hours, the mixture is treated with dichloromethane (10 ml) and extracted with water (4×25 ml). The combined aqueous extract is treated with sodium ethylenediaminetetraacetate (0.5 g), followed by sufficient solid sodium chloride to form a saturated solution. This is then extracted with dichloromethane (4×50 ml), and the combined organic extract is dried over magnesium sulphate and evaporated, to give (1R,2S)-2-(3-pyridyl)tetrahydro-2H-thiopyran 1-oxide (1.1 g), in the form of a yellow solid.

1. waitAfter a further period of four hours
2. extractionextracted with water (4×25 ml)
3. extractionThe combined aqueous extract
4. additionis treated with sodium ethylenediaminetetraacetate (0.5 g)
5. customto form a saturated solution
6. extractionThis is then extracted with dichloromethane (4×50 ml)
7. extractionthe combined organic extract
8. dry with materialis dried over magnesium sulphate
9. customevaporated

ORD record

ord-9ddac06245db45e3b301b6ee961a284a

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05688954