Ethyl 2-methylnicotinate → (2-Methylpyridin-3-yl)methanol

Ethyl 2-methylnicotinate 18-1 (257 mg) was mixed with dichloromethane (4 ml) and to the mixture at −78° C. was added dropwise 1 M diisobutyl aluminium hydride (4 ml), followed by siring for 1 hour. The reaction was quenched with methanol and to the mixture was added aqueous Rochel solution (20 ml), followed by stirring for 2 hours. The resulting mixture was extracted with dichloromethane, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was column-chromatographed (ethyl acetate/hexane=1/1) to yield the compound 18-2 (166 mg, 87%).

1. customThe reaction was quenched with methanol and to the mixture
2. additionwas added aqueous Rochel solution (20 ml)
3. extractionThe resulting mixture was extracted with dichloromethane
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was column-chromatographed (ethyl acetate/hexane=1/1)

ORD record

ord-5653aa90a8324e35aa41e36d14158de6

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071650B2