Methyl iodide → (S)-2-Methoxy-3-phenylpropanoic acid

Temperature

65 °C

(S)-2-Hydroxy-3-phenylpropanoic acid (1.0 g, 6.02 mmol) was dissolved in THF (100 ml), sodium hydride (0.48 g, 12.00 mmol) and methyl iodide (1.71 g, 12.04 mmol) were added, and the mixture was stirred at 65° C. for one hour. After leaving to cool, the reaction solution was concentrated under reduced pressure and adjusted to pH 4 by adding a 6 M aqueous hydrochloric acid solution thereto. The aqueous layer was extracted with ethyl acetate, the organic layer was concentrated, and the resulting residue was purified by column chromatography (dichloromethane:methanol=10:1) to afford the title compound (0.71 g, 59%).

1. customAfter leaving
2. temperatureto cool
3. concentrationthe reaction solution was concentrated under reduced pressure
4. additionby adding a 6 M aqueous hydrochloric acid solution
5. extractionThe aqueous layer was extracted with ethyl acetate
6. concentrationthe organic layer was concentrated
7. customthe resulting residue was purified by column chromatography (dichloromethane:methanol=10:1)

ORD record

ord-0b055f01eeec4ece90aa1dbb1d8ffac2

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409952B2