Water → HCID 19739325, compound

Participants

Reaction Steps

7 g of methoxymethyl-triphenylphosphonium chloride were suspended in 35 ml of t-butyl methyl ether and the suspension was treated at -20° C. with 2.43 g of potassium t-butylate. The mixture was stirred for a further 1 hour at room temperature, then treated dropwise at -20° C. with a solution of 2 g of 4-(1E-pentenyl)cyclohexanone in 18 ml of tetrahydrofuran and the mixture was stirred for a further 1 hour at room temperature. The reaction mixture was subsequently treated with water and extracted three times with 50 ml of diethyl ether each time. The extracts were washed with water and the wash-water was back-extracted with diethyl ether. The organic phases were dried over magnesium sulphate and freed from solvent. The residue was dissolved in ethyl acetate and the solution was diluted with petroleum ether, freed from precipitated triphenylphosphine oxide by filtration and the filtrate was concentrated. This procedure for the separation of triphenylphosphine oxide was repeated twice and the crude product of 1-(methoxymethylene)-4-(1E-pentenyl)cyclohexane obtained was processed without additional purification.

Provenance & Evidence