Methyl iodide → HCID 178495004, compound

Participants

Reaction Steps

60 ml of THF are added under an N2 atmosphere to 100 mmol of NaH in the form of an oil dispersion. The mixture is stirred vigorously and heated to 45° C.-50° C. 120 mmol of methyl iodide are then added, and 80 mmol of trans-4-(p-methoxyphenyl)cyclohexylpropyl alcohol [prepared as described above by malonic ester synthesis and reduction using LiAlH4 ] in 20 ml of THF are subsequently added dropwise over the course of 30 minutes. The mixture is subsequently stirred for a further 30 minutes at the same temperature, and the reaction mixture is then cooled and carefully hydrolyzed using aqueous THF. When the vigorous evolution of H2 is complete, the mixture is subjected to customary work-up, giving trans-4-(4-oxapentyl)-(p-methoxyphenyl)cyclohexane, C 19 N (15.1) I.

Provenance & Evidence