Imidazole → 4-(Tert-butyldimethylsilyloxymethyl)pyridine

Participants

Reaction Steps

To a solution of pyridin-4-ylmethanol (25.7 g, 0.24 mol) and imidazole (19.8 g, 0.29 mol) in dry DMF (300 mL) and dry DCM (33 mL) under nitrogen atmosphere was added TBDMSCl (42.6 g, 0.29 mol). The solution was stirred for 18 h under which time a precipitate formed. The reaction mixture was concentrated by removal of volatiles (about 100 mL) followed by addition of water (500 mL). The resulting mixture was extracted with 1:1 heptane:EtOAc (200 mL×3). The combined organic phases were washed with brine (×2), dried (MgSO4), filtered and evaporated to yield 4-((tert-butyldimethylsilyloxy)-methyl)pyridine (51.70 g, 98%) as an oil. 1H NMR (600 MHz, cdcl3) δ −0.01 (s, 6H), 0.82 (s, 9H), 4.63 (s, 2H), 7.14 (m, 2H), 8.43 (m, 2H).

Provenance & Evidence