1-(2-Chloropyridin-4-yl)ethan-1-one → 4-Pyridinemethanol, 2-chloro-.alpha.-methyl-, (.alpha.R)-

A solution of 1-(2-chloropyridin-4-yl)ethanone (7.18 g) in tetrahydrofuran (10 mL) was added dropwise to a solution of (+)-DIP-chloride (19.2 g) in tetrahydrofuran (340 mL) at −20° C., and the reaction solution was stirred at the same temperature overnight. The reaction solution was returned to room temperature, and the solvent was evaporated under reduced pressure. The residue was diluted with an ether, diethanolamine (12.1 g) was added to the diluent, and the reaction solution was stirred at room temperature for four hours. The insoluble matter was separated by filtration through celite, and the mother liquor was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (carrier: Chromatorex, elution solvent: heptane-ethyl acetate) to obtain the title compound (3.84 g). The property values of the compound are as follows.

1. customwas returned to room temperature
2. customthe solvent was evaporated under reduced pressure
3. additionThe residue was diluted with an ether, diethanolamine (12.1 g)
4. additionwas added to the diluent, and the reaction solution
5. stirringwas stirred at room temperature for four hours
6. customThe insoluble matter was separated by filtration through celite
7. concentrationthe mother liquor was concentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (carrier: Chromatorex, elution solvent: heptane-ethyl acetate)

ORD record

ord-f81b6a99299043a99474bba34c791222

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07618960B2