Oxygen → 1-Phenyl-3-heptanol

Participants

Reaction Steps

A reaction vessel (50 ml, a two-neck, eggplant type flask) is subjected to nitrogen gas purging. NaBH3CN (1.0 mmol, 62.8 mg), AIBN (0.005 mmol, 0.8 mg) and Bu2(t-Bu)SnCl (0.025 mmol, 8.1 mg, 7 μl) are added to tert-butanol (2 ml). Then, 3-iodo-1-phenylheptane (0.5mmol, 151.1mg, 115 μl) is added. The introduction of nitrogen gas is discontinued, a nitrogen gas-filled black butyl rubber balloon is set instead, and using a syringe, oxygen (0.75 mmol, 18 ml) is bubbled into the solution. Thereafter, the reaction vessel is immersed in an oil bath at 60° C. After 13 hours, heating is discontinued and the reaction mixture is diluted with pure water (10 ml) and extracted with ether (15 ml×4). The organic solution is dried over anhydrous magnesium sulfate and the solvent is distilled off. The residue is purified by column chromatography (silica gel 4 g, ethyl acetate/hexane 20%) to provide 1phenyl-3-heptanol (89.4 mg, 93%).

Provenance & Evidence