Sodium Iodide → (E)-6,10-Dimethyl-5,9-undecadien-1-yl iodide

Participants

Reaction Steps

A solution of 1.80 g (9.20 mmol) of Part A (E)-6,10-dimethyl-5,9-undecadien-1-ol in 50 mL of methylene chloride and 2.00 mL (14.3 mmol) of triethylamine at 0° C. was treated with 1.14 g (10.00 mmol) of methanesulfonyl chloride dropwise over 0.2 hours. The reaction mixture was stirred for 1.0 hour when it was quenched with saturated aqueous NH4Cl solution and diluted with ether. The organic fraction was washed with saturated NaHCO3, brine, dried (Na2SO4) and evaporated to provide a crude colorless oil. The crude mesylate (~9.0 mmol) was diluted with 50 mL of acetone and treated with 4.05 g (27.00 mmol) of NaI, refluxed for 5 hours, and cooled to room temperature. The mixture was diluted with 250 mL of ether and extracted with NaHS03, brine, dried (MgSO4) and concentrated to provide a pale yellow oil. The oil was purified by flash chromatography (180 g of silica gel) eluting with hexane to provide 2.60 g (85%) of title iodide as a colorless oil.

Provenance & Evidence