Potassium hydride → HCID 15213644, compound

To a cooled (0° C.) suspension of potassium hydride (1.58 g, 39.5 mmol) (previously washed 3 times with pentane) in tetrahydrofuran (22 mL) was added, under an argon atmosphere, a solution of methyl methylthiomethyl sulfoxide (1.36 mL, 13.04 mmol, previously dried over molecular sieves for 3 hours) in tetrahydrofuran (3 mL) over 1 hour. After stirring for a further 30 minutes, a solution of 3 (3.17 g, 13.1 mmol) in THF (2 mL) was added, at 0° C., over 1 hour. The reaction mixture was then allowed to warm up to room temperature and was stirred overnight. The mixture was quenched by addition of aqueous ammonium chloride (6 mL, 25%). After 10 minutes, the solid was filtered off and the filtrate concentrated. The residue was taken up in ether (20 mL) and 9N sulfuric acid (0.05 mL) was added. After stirring for 30 hours, saturated sodium hydrogen carbonate was added. The ether phase was separated and concentrated to 5 mL. Saturated sodium hydrogen sulphite (1.5 g) solution was added and the mixture stirred for 30 minutes. The phases were separated. The ethereal phase was stirred for further 30 minutes with a saturated sodium hydrogen sulphite (0.5 g) solution. The phases were separated, and the collected aqueous phases were treated with aqueous sodium hydroxide (5 mL, 20%) and extracted with ether. The ether phase was dried (MgSO4) and evaporated under reduced pressure to give 4 as a yellow liquid (0.16 g, 11%). δH (400 MHz; CDCl3): 3.0 (2H, m), 2.15–2.45 (6H, m), 1.65 (2H, m).

1. temperatureTo a cooled
2. washpreviously washed 3 times with pentane) in tetrahydrofuran (22 mL)
3. additionwas added, under an argon atmosphere
4. dry with materiala solution of methyl methylthiomethyl sulfoxide (1.36 mL, 13.04 mmol, previously dried over molecular sieves for 3 hours) in tetrahydrofuran (3 mL) over 1 hour
5. stirringwas stirred overnight
6. customThe mixture was quenched by addition of aqueous ammonium chloride (6 mL, 25%)
7. waitAfter 10 minutes
8. filtrationthe solid was filtered off
9. concentrationthe filtrate concentrated
10. addition9N sulfuric acid (0.05 mL) was added
11. stirringAfter stirring for 30 hours
12. additionsaturated sodium hydrogen carbonate was added
13. customThe ether phase was separated
14. concentrationconcentrated to 5 mL
15. additionSaturated sodium hydrogen sulphite (1.5 g) solution was added
16. stirringthe mixture stirred for 30 minutes
17. customThe phases were separated
18. stirringThe ethereal phase was stirred for further 30 minutes with a saturated sodium hydrogen sulphite (0.5 g) solution
19. customThe phases were separated
20. additionthe collected aqueous phases were treated with aqueous sodium hydroxide (5 mL, 20%)
21. extractionextracted with ether
22. dry with materialThe ether phase was dried (MgSO4)
23. customevaporated under reduced pressure

ORD record

ord-c6ac6282209b4379a8ea2bda0e7568a0

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07189747B2