Water → HCID 23618152, compound

Temperature

0 °C

Pyridin-4-ylmethanol (4.0 g, 37 mmol) was dissolved in dichloromethane (50 mL), and triethylamine (11.21 g, 111 mmol) was added to the reaction mixture. The solution was cooled to 0° C. and methanesulfonyl chloride (MsCl) (6.3 g, 55.5 mmol) was added slowly. After the addition was complete, the reaction was stirred at 0° C. for 15 min and then stirred at room temperature for 2 hours. Water was slowly added and the solution was extracted with dichloromethane. The organic layer was washed with brine, and dried over sodium sulfate and concentrated in vacuo. The residue was dissolved in methanol, and activated charcoal was added. After the mixture was stirred for 1 hour the mixture was filtered through a plug of celite and concentrated in vacuo to afford pyridine-4-ylmethyl methanesulfonate (49).

1. additionAfter the addition
2. stirringstirred at room temperature for 2 hours
3. extractionthe solution was extracted with dichloromethane
4. washThe organic layer was washed with brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in vacuo
7. dissolutionThe residue was dissolved in methanol
8. additionactivated charcoal was added
9. stirringAfter the mixture was stirred for 1 hour the mixture
10. filtrationwas filtered through a plug of celite and
11. concentrationconcentrated in vacuo

ORD record

ord-360df9bdf8e04354a5d9cb3d2fccae9d

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703776B2