Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | N-(7-Bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide | HCID 23113867 | — |
| Catalyst | copper(I) bromide | HCID 24593 | — |
| Solvent | Sodium methanolate methanol | HCID 23694274 | — |
| Product | HCID 11292759 | HCID 11292759 | 58.2% |
Reaction Steps
A mixture of N-(7-bromo-3-(4-isopropylphenyl)-4,6-dimethyl-2,3-dihydro-1-benzofuran-5-yl)-3,3-dimethylbutanamide (250 mg, 0.545 mmol) obtained in Example 35, copper(I) bromide (78 mg, 0.545 mmol), ethyl acetate (88 mg, 1.00 mmol), and 28% sodium methoxide-methanol solution (20 mL) was refluxed with heating for 6 hours. 1 N Hydrochloric acid was added to the reaction solution and the product was extracted with diisopropyl ether. The extracts were washed with water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) and recrystallized from hexane-ethyl acetate to obtain 130 mg (yield: 58%) of the title compound. Melting point: 191-193° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07507841B2 |
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| Source dataset | uspto-grants-2009_03 |
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| ORD ID | ord-010f1a3bfe794fca84926ac9602d5b5b |
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| Source note | uspto-grants-2009_03 |
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