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2-Chloro-3-hydroxy-6-(1-hydroxyethyl)-4-iodo-pyridine (4.49 g, 15 mmole) was dissolved in 25 ml dry dimethylformamide in an oven dried 50 ml two neck round bottom flask under nitrogen. The solution was cooled to 0° C., was treated with sodium hydride (600 mg, 15 mmole), and the mixture was stirred 1 h at room temperature. The mixture was treated with crotyl chloride (1.6 ml, 16.5 mmole) and one crystal of lithium iodide and the reaction mixture was stirred 20 h at room temperature. The reaction mixture was diluted with 100 ml ethyl acetate, was washed with 4×50 ml 50% saturated 1:1 sodium chloride/sodium bicarbonate, and was dried over anhydrous magnesium sulfate/potassium carbonate. The dried organics were concentrated in vacuo to a yellow oil which was crystallized from hexane to give 4.72 g (89%) of 3-(2-butenyloxy)-2-chloro-6-(1-hydroxyethyl)-4-iodo-pyridine as a white solid (Melting Point: 61-62.50° C.).

1. dry with materialdried 50 ml two neck round bottom flask under nitrogen
2. stirringthe reaction mixture was stirred 20 h at room temperature
3. washwas washed with 4×50 ml 50% saturated 1:1 sodium chloride/sodium bicarbonate
4. dry with materialwas dried over anhydrous magnesium sulfate/potassium carbonate
5. concentrationThe dried organics were concentrated in vacuo to a yellow oil which
6. customwas crystallized from hexane