Methanol → (5-(tert-Butyl)pyridin-3-yl)methanol

Participants

Reaction Steps

3-tert-butyl-5-((triisopropylsilyloxy)methyl)pyridine (0.7 g, 2.637 mmol) was dissolved in HCl in methanol (42 mL, 1.25M, 52.73 mmol) at room temperature and stirred for overnight. The solvent was removed under vacuum, dissolved in chloroform and washed with saturated aqueous Na2CO3. The resulting organic solvent was dried, concentrated to give a residue which was purified by flash column chromatography to give pure (5-tert-butylpyridin-3-yl)methanol (0.2 g). 1H NMR (CDCl3): d: 1.280 (s, 9H), 4.663 (s, 2H), 7.730 (s, 1H), 8.225 (s, 1H), 8.368 (s, 1H).

Provenance & Evidence