Iodine → HCID 67903394, compound

Participants

Reaction Steps

To a solution of 8.25 g (25.5 mmol) of N,N-dimethyl-2-allylhexadecanamide in THF/ H2O (1:3 v/v, 120 mL) 9.69 g (38.2 mmol) of iodine was added at room temperature and the reaction mixture was stirred for 3 days. Then, the mixture was diluted with 200 mL of ethyl acetate, washed twice with 10% sodium thiosulfate and extracted twice with ethyl acetate. The combined organic layers were dried with sodium sulfate and after evaporation of the solvent it was obtained 11.3 g of a solid that was purified by column chromatography (silica gel, hexane: ethyl acetate 7%) to give 6.98 g of the trans isomer, 0.91 g of a mixture of the cis and trans isomers and 0.42 g of the cis isomer (overall yield 87%).

Provenance & Evidence