Triethylamine → HCID 22502863, compound

5-Bromo-2-(3-hydroxy-1-butynyl)pyridine (5.426 g) was dissolved in tetrahydrofuran (60 ml), followed by the sequential addition of triethylamine (10 ml) and methanesulfonyl chloride (2.2 ml) under ice-cooling, and the resulting mixture was stirred for 1 hr. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was dissolved in methanol (16 ml), and under ice-cooling, 28% sodium methoxide/methanol solution (4.6 ml) was added thereto and the resulting mixture was stirred at room temperature overnight. The reaction mixture was evaporated and partitioned between ethyl acetate and water. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a brown oil (1.968 g, yield; 34%).

1. temperaturecooling
2. customThe reaction mixture was partitioned between ethyl acetate and water
3. washThe organic layer was washed with water
4. dry with materialdried (over MgSO4)
5. customevaporated
6. dissolutionThe resulting residue was dissolved in methanol (16 ml)
7. temperatureunder ice-cooling
8. addition28% sodium methoxide/methanol solution (4.6 ml) was added
9. stirringthe resulting mixture was stirred at room temperature overnight
10. customThe reaction mixture was evaporated
11. custompartitioned between ethyl acetate and water
12. washThe resulting organic layer was washed with water
13. dry with materialdried (over MgSO4)
14. customevaporated
15. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

ORD record

ord-bfbbd366e54e4fb6a9a9bbd506942547

Source dataset

uspto-grants-2002_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06340759B1