Ammonium Chloride → HCID 45116455, compound

To a suspension of (methoxymethyl)triphenylphosphonium chloride (4.65 g) in tetrahydrofuran (20 ml) was added dropwise potassium tert-butoxide (1.0 M solution in tetrahydrofuran) (14.6 ml) on an ice bath under a nitrogen atmosphere, the solution was stirred for 20 minutes, then a solution of 6-bromopyridine-3-carbaldehyde (2.1 g) in tetrahydrofuran (16 ml) was added dropwise thereto followed by stirring overnight at room temperature. A saturated aqueous solution of ammonium chloride was added thereto followed by stirring, the solution was extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. Obtained by purifying the residue by NH silica gel column chromatography (hexane-ethyl acetate system), 2-bromo-5-(2-methoxyvinyl)pyridine (2.2 g) was stirred in acetone (20 ml), water (10 m) and concentrated sulfuric acid (1 ml) were sequentially added thereto, the solution was stirred for 1.5 hours at 80° C., and then neutralized with a saturated aqueous solution of sodium bicarbonate. The solution was extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo to provide the title compound (1.5 g).

1. stirringby stirring overnight at room temperature
2. stirringby stirring
3. extractionthe solution was extracted with ethyl acetate
4. washsequentially washed with water and brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customthe solvent was evaporated in vacuo
7. customObtained
8. customby purifying the residue by NH silica gel column chromatography (hexane-ethyl acetate system), 2-bromo-5-(2-methoxyvinyl)pyridine (2.2 g)
9. stirringwas stirred in acetone (20 ml)
10. additionwater (10 m) and concentrated sulfuric acid (1 ml) were sequentially added
11. stirringthe solution was stirred for 1.5 hours at 80° C.
12. extractionThe solution was extracted with ethyl acetate
13. washsequentially washed with water and brine
14. dry with materialdried over anhydrous magnesium sulfate
15. customthe solvent was evaporated in vacuo

ORD record

ord-b957e4f164f74696aca975d83f0b4be5

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07960412B2