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

Prepared according to a slightly modified procedure of I. M. Bell et al., J. Med. Chem. 41, 2146–2163 (1998). To a stirred solution of ethyl 2-methylnicotinate (2.0 g, 12.1 mmol) in tetrahydrofuran (40 mL) cooled to 0° C. was slowly added a 1 M solution of diisobutyl aluminum hydride in tetrahydrofuran (30 mL, 30 mmol). After 5 minutes, the reaction was quenched with saturated aqueous sodium bicarbonate and saturated aqueous sodium potassium tartrate. The aqueous phase was repeatedly extracted with chloroform. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 2.5 g of the crude title compound as a yellow oil. The crude material was used as such in the next step.

1. customPrepared
2. customthe reaction was quenched with saturated aqueous sodium bicarbonate and saturated aqueous sodium potassium tartrate
3. extractionThe aqueous phase was repeatedly extracted with chloroform
4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-322a230ae2a64fceb63ec0a1888afabb

Source dataset

uspto-grants-2006_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07064120B2