Triethylamine → HCID 53677948, compound

5-Bromo-2-(3-hydroxy-1-propenyl)pyridine (3.718 g) was dissolved in tetrahydrofuran (60 ml), followed by the sequential addition of triethylamine (7.1 ml) and methanesulfonyl chloride (1.6 ml) under ice-cooling, and the resulting mixture was stirred as it was, for 25 min. After the resulting insoluble matters were filtered off, the mixture was evaporated. The resulting residue was dissolved in ethanol (60 ml), followed by the addition of sodium ethoxide (1.388 g)/ethanol (25 ml) solution under ice-cooling, and the mixture was stirred at room temperature for 3.5 hr. The reaction mixture was evaporated, and the resulting residue was 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 yellow oil (2.607 mg, yield; 65%).

1. temperaturecooling
2. filtrationAfter the resulting insoluble matters were filtered off
3. customthe mixture was evaporated
4. dissolutionThe resulting residue was dissolved in ethanol (60 ml)
5. additionfollowed by the addition of sodium ethoxide (1.388 g)/ethanol (25 ml) solution under ice-
6. temperaturecooling
7. stirringthe mixture was stirred at room temperature for 3.5 hr
8. customThe reaction mixture was evaporated
9. customthe resulting residue was partitioned between ethyl acetate and water
10. washThe resulting organic layer was washed with water
11. dry with materialdried (over MgSO4)
12. customevaporated
13. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

ORD record

ord-3159f3780540453e929beee503c2b961

Source dataset

uspto-grants-2004_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06790844B2