Iodine → [1-Cyano-2-(tetrahydro-pyran-4-yl)-hex-5-enyl]-phosphonic acid diethyl ester

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Reaction Steps

In a reaction flask, Mg (5.7 g) was placed in THF (50 mL) with an iodine chip. The reaction mixture was stirred vigorously, as 4-bromobutene (25 mL) was added. The reaction mixture was then heated slightly. After consumption of the Mg metal, the reaction mixture was cannulated into a flask containing a mixture of [1-cyano-2-(tetrahydro-pyran-4-yl)-vinyl]-phosphonic acid diethyl ester (21.78 g, 79.7 mmol) and CuI (0.3 g) in THF (30 mL). The reaction mixture was stirred for three hours and then worked up with saturated aqueous NH4Cl and ethyl acetate. The layers were separated, and the organic layer was dried with MgSO4, filtered, and evaporated in vacuo to yield the title compound as an oil.

Provenance & Evidence