Sodium Iodide → 2-Chloro-3-(3-methyl-2-butenyloxy)-6-(1-hydroxyethyl)-4-iodo-pyridine

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Reaction Conditions

Reaction Steps

2-Chloro-3-hydroxy-6-(1-hydroxyethyl)-4-iodo-pyridine (2.99 g, 10 mmole) was dissolved in 15 ml dry dimethylformamide in an oven dried 100 ml two neck round bottom flask under nitrogen. The solution was cooled to 0° C., was treated with sodium hydride (400 mg, 10 mmole), and the mixture was stirred 1 h at room temperature. The mixture was treated with 1-chloro-3-methyl-2-butene (1.2 ml, 11 mmole) and sodium iodide (150 mg, 1 mmole) and the reaction mixture was stirred 18 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 potassium carbonate. The dried organics were concentrated in vacuo to a yellow oil which was crystallized from 25 ml hexane to give 3.2 g (87%) of 2-chloro-3-(3-methyl-2-butenyloxy)-6-(1-hydroxyethyl)-4-iodo-pyridine as an off-white solid, Melting Point: 80-81° C.

Provenance & Evidence