Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Hexane | HCID 8058 | — |
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | HCID 23116478 | HCID 23116478 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 11995949 | HCID 11995949 | 61% |
Reaction Steps
Methyl 3,5-diallyloxy-2-(4-methoxybenzoyl)phenylacetate (100 mg, 0.25 mmol) obtained in Example 15, Step 1 was dissolved in dichloromethane (10 mL). After the solution was cooled to −78° C., a 1.0 mol/L solution of boron tribromide in hexane (0.50 mL, 0.5 mmol) was added thereto, followed by stirring at −78° C. for 30 minutes. To the reaction mixture were successively added methanol and a saturated aqueous solution of sodium hydrogencarbonate, followed by extraction with chloroform. The organic layer was dried anhydrous over sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by preparative thin layer chromatography (chloroform/methanol=20/1) to obtain Compound 18 (54 mg, 61%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07538224B2 |
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| Source dataset | uspto-grants-2009_05 |
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| ORD ID | ord-399eabf9e3634ca69559ce8e9d3c9377 |
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| Source note | uspto-grants-2009_05 |
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