Methoxymethyl-triphenylphosphonium chloride → 1-[4-(Methoxymethylene)cyclohexyl]-4-[2-(4-propylcyclohexyl)ethyl]-benzene

Participants

Reaction Steps

THF solution (20 ml) including methoxymethyltriphenylphosphonium chloride (2 g, 5.9 mmol) was slowly added by in solid potassium tert-butoxide (0.6 g, 5.9 mmol) for 3 minutes in a flask filled with argon gas at −10° C. and then stirred for 20 minutes with maintaining the temperature. The temperature of reacting solution was adjusted to 0° C., added slowly dropwise by THF solution (15 ml) of 4-{4-[2-(4-propylcyclohexyl)ethyl]phenyl}cyclohexanone (1.5 g, 4.5 mmol) and then was stirred by warming to a room temperature. After the reaction termination, the resulting solution was diluted by distilled water (20 ml), extracted by ether (20 ml×3 times), washed by distilled water (10 ml×2 times) and then concentrated under reduced pressure. The residue was purified by column chromatography (ethyl acetate:petroleum ether=1:40) to obtain 1-[4-(methoxymethylene)cyclohexyl]-4-[2-(4-propylcyclohexyl)ethyl]-benzene (1.2 g, 80%).

Provenance & Evidence