Water → HCID 178420907, compound

9.7 g (173 mmol) of potassium hydroxide and 17.5 g (173 mmol) of 3-mercapto-1,2,4-triazole were dissolved in 200 ml of methanol and heated under reflux for one hour. After the solvent had been distilled off under reduced pressure, the residue was dried by azeotropic distillation with toluene and then taken up in 300 ml of methanol. 33.6 g (173 mmol) of tetrahydropyran-2-ylmethyl methanesulfonate (step a) were then added and the mixture was stirred at room temperature for 24 hours. 200 ml of water and 200 ml of methyl tert-butyl ether were then added to the reaction mixture and the organic phase was separated off, washed with water and dried. The mixture was concentrated and the residue was chromatographed over silica gel, yielding 18.2 g (53% of theory) of a yellow oil. (1H-NMR (CDCl3; δ in ppm): 8.05 (s,1H); 4.15 (d,1H); 3.65 (m,1H); 3.50 (m,1H); 3.25-3.10 (m,2H); 1.85 (m,1H); 1.75-1.25 (m,6H))

1. temperatureheated
2. temperatureunder reflux for one hour
3. distillationAfter the solvent had been distilled off under reduced pressure
4. dry with materialthe residue was dried by azeotropic distillation with toluene
5. customthe organic phase was separated off
6. washwashed with water
7. customdried
8. concentrationThe mixture was concentrated
9. customthe residue was chromatographed over silica gel
10. customyielding 18.2 g (53% of theory) of a yellow oil

ORD record

ord-9cd1dde2f24c4884b9be4c8e9c0d13bd

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06265352B1