Hydrochloric Acid → (R)-methyl 2-(quinolin-8-yloxy)propanoate

Temperature

25 °C

To a stirred mixture of quinolin-8-ol (300 mg, 2.07 mmol) in THF (5 mL) was added (S)-methyl 2-hydroxypropanoate (215 mg, 2.07 mmol), PPh3 (647 mg, 2.47 mmol) and DEAD (430 mg, 2.47 mmol). The mixture was stirred at 25° C. for 16 hours. Subsequently, 1M HCl was added (10 mL) and the solution was washed with EtOAc (20 mL×3). The pH of the aqueous solution was raised by addition of aqueous NaHCO3 (10 mL), and then this solution was washed with EtOAc (10 mL×3). The combined organic extracts were washed with brine (20 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by silica column chromatography to afford the product as a colorless oil (300 mg, 62.5% yield). LCMS (m/z): 233.1 [M+H]+

1. washthe solution was washed with EtOAc (20 mL×3)
2. temperatureThe pH of the aqueous solution was raised by addition of aqueous NaHCO3 (10 mL)
3. washthis solution was washed with EtOAc (10 mL×3)
4. washThe combined organic extracts were washed with brine (20 mL)
5. dry with materialdried over anhydrous Na2SO4
6. concentrationconcentrated
7. customThe residue was purified by silica column chromatography

ORD record

ord-3680be9ad3424917af87f96d1da27ac3

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266836B2