HuagongsheHuagongshe Chemistry Print Report · For research reference only
Boron Trichloride → Phenoxodiol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Boron Trichloride | HCID 25135 | — |
| Reactant | 7-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran | HCID 59592104 | — |
| Reactant | n-Bu4NI BCl3 | HCID 87695880 | — |
| Product | Phenoxodiol | HCID 219100 | — |
| Product | 7-hydroxy-3-(4-methoxyphenyl)-2H-1-benzopyran | HCID 9859847 | — |
Reaction Steps
As shown in Scheme 2, 7-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran (compound 1) was reacted with n-Bu4NI/BCl3 and BCl3 to give haginin E (compound 2a) at a yield of 79% and 7-hydroxy-3-(4-methoxyphenyl)-2H-1-benzopyran (4′-O-methyl haginin E, compound 2b) at a yield of 81%, respectively. Treatment of compound 1 with Pd(OH)2/C (Pearlman's reagent) and cyclohexene in refluxing ethanol promoted O-debenzylation and reduction of the chromene ring in one step, giving 7-hydroxy-3-(4-methoxyphenyl)-1-benzopyran (compound 3a) at a yield of 94%. Compound 3a was subsequently demethylated by use of n-Bu4NI/BCl3 to give equol (compound 3b) at a yield of 95%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07875735B2 |
| Source dataset | uspto-grants-2011_01 |
| ORD ID | ord-2c0a2f50646b4bbf9ab554ce961b1ec4 |
| Source note | uspto-grants-2011_01 |