Potassium Carbonate → HCID 90202452, compound

Participants

Reaction Steps

5-Hydroxy-2-methylpyridine (available from Aldrich Chemical Company, Inc., 1001 West Saint Paul Avenue, Milwaukee, Wis. 53233, USA; 5.00 g, 45.8 mmol) was dissolved in DMF (90 mL) and K2CO3 (6.9 g, 50 mmol) and tetrabutylammonium iodide (2 g, 5.4 mmol) were added. 2-Chlorobenzyl chloride (6.4 mL, 50.6 mmol) was added and the mixture was stirred at room temperature for 20 h. The reaction mixture was partitioned between EtOAc (300 mL) and H2O (300 mL). The organic layer was dried (Na2SO4), filtered, evaporated, and purified by chromatography (30% EtOAc/hexane) to give 5-(2-chloro-benzyloxy)-2-methyl-pyridine (7.00 g, 66%) as a yellow oil.

Provenance & Evidence