Imidazole → 5-((Tert-butyldimethylsilyloxy)methyl)-2-fluoropyridine

Participants

Reaction Steps

(6-Fluoropyridin-3-yl)methanol (9.54 g, 75.0 mmol) and imidazole (5.11 g, 75.0 mmol) were placed into a round-bottomed flask with CH2Cl2 (300 mL). tert-butyldimethylsilyl chloride (10.9 g, 72.8 mmol) was dissolved in CH2Cl2 (75 mL) and added drop-wise to the reaction mixture, which was then allowed to stir overnight at rt. The reaction was quenched by adding water (100 mL). The biphasic mixture was then separated and the aqueous layer was washed with CH2Cl2 (2×30 mL). The combined organic layer was then washed with H2O (3×50 mL), brine (50 mL), dried over MgSO4, filtered, and concentrated to give 5-((tert-butyldimethylsilyloxy)methyl)-2-fluoropyridine as a yellow oil, which was used in the next step without further purification.

Provenance & Evidence