Tetrahydrofuran → HCID 178444448, compound

Participants

Reaction Steps

A mixture of 4.0 g of [3-(4-[tetrahydro-2-pyranyloxy]phenyl)-1-propyl]triphenylphosphonium bromide, 1.3 g of trans-4-pentylcyclohexanecarboxaldehyde and 50 ml of absolute tetrahydrofuran was treated portionwise with 0.8 g of solid potassium t-butylate. After completion of the addition the reaction mixture was stirred for a further two hours and then poured into 500 ml of water and extracted three times with 100 ml of diethyl ether each time. The organic phases were washed twice with 500 ml of concentrated sodium chloride solution each time, dried over magnesium sulphate, filtered and subsequently concentrated. Chromatography of the residue on silica gel with toluene gave 1.0 g of 1-[tetrahydro-2-pyranyloxy]-4-[4-(trans-4-pentylcyclohexyl)-3-butenyl]benzene (cis/trans mixture).

Provenance & Evidence