Ethyl 3-cyclopropyl-3-(2-((methoxymethoxy)methyl)pyridin-4-yl)acrylate → Ethyl 3-cyclopropyl-3-(2-(hydroxymethyl)pyridin-4-yl)propanoate

To a solution of ethyl 3-cyclopropyl-3-(2-((methoxymethoxy)methyl)pyridin-4-yl)acrylate (1.28 g) in acetic acid (20 mL) was added zinc powder (2.87 g) at 20° C., and the mixture was stirred at room temperature for 10 min. The reaction mixture was filtered, and the solvent of the filtrate was evaporated under reduced pressure. The residue was dissolved in THF (30 mL), and conc. sulfuric acid (3.51 mL) was added. The reaction mixture was stirred at 60° C. for 1 hr, and further heated under reflux for 5 min. The reaction mixture was basified with aqueous potassium carbonate solution at 0° C., and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (626 mg) as a colorless oil.

1. filtrationThe reaction mixture was filtered
2. customthe solvent of the filtrate was evaporated under reduced pressure
3. dissolutionThe residue was dissolved in THF (30 mL)
4. additionconc. sulfuric acid (3.51 mL) was added
5. stirringThe reaction mixture was stirred at 60° C. for 1 hr
6. temperaturefurther heated
7. temperatureunder reflux for 5 min
8. customwas basified with aqueous potassium carbonate solution at 0° C.
9. extractionextracted with ethyl acetate
10. washThe extract was washed with water and saturated brine
11. dry with materialdried over anhydrous magnesium sulfate
12. customThe solvent was evaporated under reduced pressure
13. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORD record

ord-e5873646428740499fa6ac2b8fff41df

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382188B2