Sodium Iodide → 5-Ethyl-2-pyridinol

Temperature

65 °C

To a solution of 2-methoxy-5-vinyl-pyridine (2 g) in anhydrous MeOH was added Pd/C (10 wt %, 100 mg). The mixture was stirred under H2 atmosphere for 5 hours before it was filtered through a pad of celite. The solvent was removed in vacuo and the residue was taken directly into next step without further purification. The crude product from previous step was dissolved in anhydrous MeCN. To this solution was added NaI (3.3 g, 21.9 mmol) and TMSCl (2.8 mL, 21.9 mmol). The resulting mixture was heated to 65° C. for 5 hours before it was filtered through a pad of celite. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography to afford the desired product (1.5 g, 83% yield). 1H NMR (300 MHz, CDCl3): δ 1.17 (t, J=7.5 Hz, 3 H), 2.39-2.49 (m, 2 H), 6.50-6.58 (m, 1 H), 7.15 (s, 1 H), 7.35-7.45 (m, 1 H).

1. filtrationwas filtered through a pad of celite
2. customThe solvent was removed in vacuo
3. customthe residue was taken directly into next step without further purification
4. dissolutionThe crude product from previous step was dissolved in anhydrous MeCN
5. filtrationwas filtered through a pad of celite
6. concentrationThe filtrate was concentrated in vacuo
7. customthe residue was purified by flash column chromatography

ORD record

ord-145426b7ca634c2ebbb38fedf0c89556

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268835B2