Diethyl Ether → HCID 19926473, compound

Participants

Reaction Steps

A mixture of 4-chloro-3-hydroxyethoxy-2-methylpyridine (1.03g, 0.0055 mol) and NaH (55% in oil, 599 mg, 0.0138 mol) in 600 ml THF was refluxed for 15 h. Excess NaH was destroyed with 3 ml of H2O. The solvent was evaporated and the residue partitioned between 100 ml 1M HCl and 100 ml CH2Cl2. The aqueous layer was collected, washed once more with 100 ml CH2Cl2 and then treated with Na2CO3 until the pH was ≈10. The aqueous layer was extracted with 150+100 ml CH2Cl2. The two latter organic layers were combined, dried over MgSO4, and evaporated leaving 720 mg enriched product. Chromatography (silica gel, diethyl ether) furnished 0.49 g (59%) pure product.

Provenance & Evidence