Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | O-Cresol | HCID 335 | — |
| Reactant | Boron trifluoride etherate | HCID 8000 | — |
| Reactant | 6-(1-Ethyl-1-hydroxy-propyl)-benzo[b]thiophene-2-carboxylic acid ethyl ester | HCID 57835388 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 57835400 | HCID 57835400 | 92% |
Reaction Steps
To a mixture of 6-(1-ethyl-1-hydroxy-propyl)-benzo[b]thiophene-2-carboxylic acid ethyl ester (0.650 g, 2.23 mmol and o-cresol (0.480 g, 4.45 mmol) in CH2Cl2 (20 mL) at −78° C. is added BF3-Et2O (0.316 g, 2.23 mol). After stirring for 10 min, the reaction mixture is allowed to warm to 0° C. over 30 min. The reaction is quenched with water (15 mL) and extracted with EtOAc (2×50 mL). The organic layer is dried over Na2SO4, concentrated, and purified by silica gel column chromatography to give the title compound (0.780 g, 92%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07897789B2 |
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| Source dataset | uspto-grants-2011_03 |
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| ORD ID | ord-eb4ddd1739a745308038402d729c1bb6 |
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| Source note | uspto-grants-2011_03 |
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