Boron tribromide → HCID 53667928, compound

Participants

Reaction Steps

At -78° C., 0.3 ml of boron tribromide was added to a solution of 0.68 g of methyl 4-methoxy-3-[1-(4-methyl-2-oxo-3-oxabicyclo[2.2.2]octanyl)methoxy]cinnamate (Example 50) in 10 ml of methylene chloride. The solution was reacted for 15 minutes, as it was. After reaction, 30 ml of an aqueous ammonium chloride solution was added to the reaction solution. The solution was extracted three times with 30 ml of ethyl acetate. The organic layer obtained was washed three times with an aqueous sodium chloride solution and was dried over magnesium sulfate. Thereafter, the solvent was removed in vacuo, yielding 0.21 g of methyl 4-hydroxy-3-[1-(4-methyl-2-oxo-3-oxabicyclo[2.2.2]octanyl)methoxy]cinnamate (a compound of the present invention) as a pale yellow oil, which had the following physiochemical properties:

Provenance & Evidence