1-(4-Fluoro-3-methoxyphenyl)ethanone → (αR)-4-Fluoro-3-methoxy-α-methylbenzenemethanol

Temperature

-20 °C

A solution of 4-fluoro-3-methoxyacetophenone (1 g) in THF (10 mL) was added dropwise to a solution of (+)-DIPCl™ (2.29 g) in THF (30 mL) in a nitrogen atmosphere at −20° C., and the reaction solution was stirred at −20° C. for 5 hours. The reaction solution was heated to room temperature, and the solvent was evaporated under reduced pressure. The residue was diluted with an ether, diethanolamine (1.25 mL) was added to the diluent, and the reaction solution was stirred at room temperature overnight. The reaction solution was filtered on a celite, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 918 mg of the title compound. The physical properties of the compound are as follows.

1. temperatureThe reaction solution was heated to room temperature
2. customthe solvent was evaporated under reduced pressure
3. additionThe residue was diluted with an ether, diethanolamine (1.25 mL)
4. additionwas added to the diluent, and the reaction solution
5. stirringwas stirred at room temperature overnight
6. filtrationThe reaction solution was filtered on a celite
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

ORD record

ord-00293c8c80b54138a1cbb32f183decee

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07880009B2