Lithium amide → 2H-Pyran, tetrahydro-2-(9-tetradecyn-1-yloxy)-

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Reaction Steps

A mixture of 7.4 g of compound IV, 1.0 g lithium amide, and 50 ml of dry, purified dioxane was stirred and refluxed 3.5 hours under nitrogen, cooled, 4.5 g of n-butyl bromide was added dropwise and the refluxing and stirring continued for 20 hours more. The mixture was chilled in an icebath, diluted with 60 ml of water and the layers separated. The aqueous layer was extracted three times with ether, the combined organic phase was washed three times with saturated NaCl solution, the solvents were evaporated and the residue distilled to give 3.2 g (36%) of compound V which boiled at 120°-123° (0.03 mm), ND25 1.4634.

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