Ethyl 2,6-dimethylnicotinate → (2,6-Dimethylpyridin-3-yl)methanol

Temperature

0 °C

To a solution of ethyl 2,6-dimethylnicotinate (1.0 g, 5.6 mmol) in THF (20 mL) at 0° C. was added LiAlH4 (318 mg, 8.4 mmol). The resulting mixture was stirred at 0° C. for 5 min and then warmed to room temperature for 1 hour. Quenched with 0.3 mL water, 0.3 mL 15% NaOH solution and then with 1 mL water sequentially. After stirred at room temperature for 15 min, sodium sulfate was added to the mixture and stirred for another 15 min and then filtered. The resulting solution was concentrated to afford the crude product which was used for next step directly without further purification. LCMS (ESI) m/z=138.1 138.1 (M+H)+.

1. temperaturewarmed to room temperature for 1 hour
2. customQuenched with 0.3 mL water, 0.3 mL 15% NaOH solution
3. stirringAfter stirred at room temperature for 15 min
4. additionsodium sulfate was added to the mixture
5. stirringstirred for another 15 min
6. filtrationfiltered
7. concentrationThe resulting solution was concentrated

ORD record

ord-320884b0c7b94f92985f0c5481abe8f9

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09353104B2