Iodine → HCID 23295948, compound

Participants

Reaction Steps

This example illustrates a synthesis of 1-(13,14-Oxidotetradecyl)-3,7-dimethylxanthine (inventive compound no. 3503). To a suspension of magnesium (1.86 g, 77.2 mmol) and a crystal of iodine in THF (20 mL) was added 10-undecenyl bromide (6.00 g, 25.8 mmol) in THF (14 mL) over 40 minutes and the reaction stirred for a further 30 minutes after the addition was complete. The solution was added via a canula over 50 minutes to a suspension of copper iodide (0.50 g, 2.58 mmol) and 1-bromo-3-chloropropane (3.84 mL, 38.7 mmol) in THF (20 mL) and stirred at 25° C. for 16 hours. Sulfuric acid (1.0M, 50 mL) was added, extracted with diethyl ether (2×60 mL) and the organic solvent dried using magnesium sulfate and evaporated. The residue was distilled at 0.25 mmHg to obtain 3.06 g (51% yield, b.p. 98°-100° C.)13-tetradecenyl chloride as a colourless liquid.

Provenance & Evidence