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

Participants

Reaction Conditions

Reaction Steps

To a solution 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), DEAD (430 mg, 2.47 mmol) and the resulting mixture was stirred at 25° C. for 16 h. Aqueous HCl (1M, 10 mL) was added, the mixture separated, and the aqueous layer extracted with ethyl acetate. The aqueous portion was basified by addition of saturated aqueous NaHCO3 (20 mL) and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography. (300 mg, yield 63%) MS (ESI+) e/z: 232.1 [M+1]+.

Provenance & Evidence