Vanillin → Allyl 4-[3-methoxy-4-(2-tetrahydropyranyloxy)cinnamoyl]-1-methyl-1-cyclohexanecarboxylate

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Reaction Steps

A solution of 1.5 g of 3-methoxy-4-(2-tetrahydropyranyloxy)benzaldehyde, derived from vanillin by the introduction of tetrahydropyranyl group thereinto, 1.5 g of allyl 4-acetyl-1-methyl-1-cyclohexanecarboxylate (Example 37), and 8 ml of sodium hexamethyldisilazide (THF 1M solution), mixed in 50 ml of THF, was reacted for 4 hours under an argon stream, while it was refluxed. After reaction, 100 ml of an aqueous ammonium chloride solution was added to the reaction solution. The solution was extracted three times with 50 ml of ethyl acetate. The organic layer obtained was washed three times with an aqueous sodium chloride solution and dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo. The oily substance obtained was subjected to column chromatography using 50 g of silica gel. From the fraction eluted with hexane and ethyl acetate=4:1, the solvent was removed in vacuo, yielding 1.1 g of allyl 4-[3-methoxy-4-(2-tetrahydropyranyloxy)cinnamoyl]-1-methyl-1-cyclohexanecarboxylate (a compound of the present invention) as a yellow oil, which had the following physiochemical properties:

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