HuagongsheHuagongshe Chemistry Print Report · For research reference only
4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole → 4-hydroxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole | HCID 10638039 | — |
| Reactant | Boron tribromide dichloromethane | HCID 22277759 | — |
| Solvent | Ethyl acetate hexane | HCID 21226206 | — |
| Product | 4-hydroxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole | HCID 10493529 | 71% |
Reaction Steps
By the method used in Example 1, Part D, 1.17 g (3.9 mmol) of 4-methoxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole was O-demethylated by treating it with 15.6 mL of 1M BBr3 /CH2Cl2 to give a material that was chromatographed on silica gel (eluted with 20% EtOAc/hexane then 50% EtOAc/hexane) to give 796 mg (71% yield) of 4-hydroxy-2-methyl-1-[(1-naphthalenyl)methyl]-1H-indole.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05733923 |
| Source dataset | uspto-grants-1998_03 |
| ORD ID | ord-ac45098226724296a2030ef33a83f824 |
| Source note | uspto-grants-1998_03 |