Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | O-Cresol | HCID 335 | — |
| Reactant | Boron trifluoride etherate | HCID 8000 | — |
| Reactant | HCID 57810594 | HCID 57810594 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 57810551 | HCID 57810551 | 91.4% |
Reaction Steps
To a mixture of 2-(1-ethyl-1-hydroxy-propyl)-benzofuran-5-carboxylic acid methyl ester (6.01 g, 22.9 mmol) and o-cresol (3.71 g, 34.4 mmol) in CH2Cl2 (150 mL) at −78° C. is added BF3-Et2O (1.63 ml, 11.5 mol). After stirring for 5 min, the reaction mixture is allowed to warm up to 0° C. over 30 min. The reaction is quenched with water (50 mL) and extracted with CH2Cl2 (50 mL). The organic layer is dried over Na2SO4, concentrated, purified on column chromatography (15-20% EtOAc/Hex) to afford the title compound (7.38 g, 91%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07579488B2 |
|---|
| Source dataset | uspto-grants-2009_08 |
|---|
| ORD ID | ord-5c90ec54c5b44d88adc24d591789c268 |
|---|
| Source note | uspto-grants-2009_08 |
|---|