HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 3-(3', 4'-Dimethoxybenzoyl)-2-(4'-methoxyphenyl)-6-methoxybenzo[b]thiophene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Veratroyl chloride | HCID 77070 | — |
| Reactant | 6-Methoxy-2-(4-methoxyphenyl)benzo[b]thiophene | HCID 850941 | — |
| Reactant | Aluminum(III) Chloride | HCID 6451240 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 3-(3', 4'-Dimethoxybenzoyl)-2-(4'-methoxyphenyl)-6-methoxybenzo[b]thiophene | HCID 10071593 | 76% |
Reaction Steps
To a well stirred solution of 2-(4'-methoxyphenyl)-6-methoxybenzo[b]thiophene (0.327g, 1.21 mmol) and 3,4-dimethoxybenzoyl chloride (0.557 g, 2.77 mmol) in CH2Cl2 (20 ml) was added AlCl3 (0.616 g, 4.62 mmol) portion-wise over a 15 minute period. After 7 hours, water was added, and the product was isolated initially by extraction with CH2Cl2 and subsequently by extraction with EtOAc. The organic layers were separately washed with brine and then combined and dried over MgSO4. Purification by flash chromatography (silica gel, 60:40 Et2O/hexanes) afforded the title compound (0.402 g, 0.92 mmol, 76%) as a pale yellow solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05886025 |
| Source dataset | uspto-grants-1999_03 |
| ORD ID | ord-00b376935c394c628d100a9fea0f81fd |
| Source note | uspto-grants-1999_03 |