反応 #342070

反応方程式

compound 1

7-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran

chroman-4-ol

Compound 4

chroman-4-ol

2,3-dichloro-5,6-dicyanobenzoquinone

compound 4

chroman-4-ol

→

compound 5

isoflavone

溶媒

1,4-dioxane

反応条件

実験手順

Using the general procedure of hydroboration-oxidation, compound 1 was converted into a chroman-4-ol (compound 4) at a yield of 60%. Compound 4 was treated with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) in refluxing 1,4-dioxane to undergo oxidation-dehydrogenation to give an isoflavone (compound 5) at a yield of 78%. After the deprotection of compound 5 with AlCl3/EtSH, daidzein (compound 6a) was produced at a yield of 92%. On the other hand, compound 5 could be selectively debenzylated with Pearlman's reagent to give formononetin (compound 6b) at a yield of 94%,

出典