Iodoethane → HCID 21468090, compound

Participants

Reaction Steps

850 mg (2.44 mmole) of 2-(1-hydroxy-4-methylpentyl)-1,4,5,8-tetramethoxynaphthalene and 510 mg (12.2 mmole) of sodium hydride (55% dispersion in oil) were dissolved in 10 ml of dry tetrahydrofuran and 1.9 g (12.2 mmole) of iodo-ethane was added thereto under nitrogen gas and then the mixture was refluxed for 3 hours. After adding 20 ml of ice water, the reaction mixture was extracted twice with dichloromethane, dried over anhydrous magnesium sulfate and filtered through a filter paper. The filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (silica gel 2.5×15 cm) using the solvent condition which increases the amount of ethylacetate so that the n-hexane/ethylacetate ratio can vary from 10:1 to 1:1, to obtain 780 mg of the title compound as a pale yellow oil.

Provenance & Evidence