Salicylaldehyde → Methyl (7E)-8-{2-[(4-cyclohexylbenzyl)oxy]phenyl}-6-oxo-7-octenoate

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Reaction Steps

Under argon, a solution of 3.00 g (10.19 mmol) of methyl 7-(diethoxyphosphoryl)-6-oxo-heptanoate XIIb in 10 ml of THF was added dropwise to a suspension of 0.25 g (10.19 mmol) of sodium hydride in 20 ml of THF. After 30 min, a solution of 2.50 g (8.49 mmol) of 2-[(4-cyclohexylbenzyl)oxy]benzaldehyde (obtainable from salicylaldehyde and 4-cyclohexylbenzyl chloride in 10 ml of THF was added dropwise. The mixture was stirred at room temperature for 2 days. Water was added, the mixture was extracted with ethyl acetate and the combined organic phases were dried over Na2SO4. The product was purified chromatographically (silica gel, cyclo-hexane/ethyl acetate 10:1).

Provenance & Evidence