Tetrahydrofuran → 4-Bromo-α-methyl-2-pyridinemethanol

Temperature

-78 °C

An oven-dried flask was cooled under argon, and to it was added 4-bromopicolinaldehyde (2.98 g, 16 mmol) and anhydrous THF (50 mL). The mixture was cooled to −78° C., and 3M methylmagnesium bromide in Et2O (6.4 mL) was added dropwise. The mixture was then allowed to warm slowly to room temperature, whereupon it was quenched with saturated NH4Cl solution. The aqueous layer was extracted with EtOAc, dried over Na2SO4, concentrated, and purified by column chromatography (gradient 0 to 60% EtOAc in hexanes) to give the product. 1H NMR (400 MHz, CDCl3) δ 8.36 (d, J=5.3 Hz, 1H), 7.57-7.48 (m, 1H), 7.38 (dd, J=5.3, 1.4 Hz, 1H), 4.88 (q, J=6.6 Hz, 1H), 3.84 (br s, 1H), 1.51 (d, J=6.6 Hz, 3H).

1. temperatureAn oven-dried flask was cooled under argon
2. temperatureto warm slowly to room temperature, whereupon it
3. customwas quenched with saturated NH4Cl solution
4. extractionThe aqueous layer was extracted with EtOAc
5. dry with materialdried over Na2SO4
6. concentrationconcentrated
7. custompurified by column chromatography (gradient 0 to 60% EtOAc in hexanes)
8. customto give the product

ORD record

ord-cec0865654264cfe89ce1180cf809a46

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987250B2