Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Water | HCID 962 | — |
| Edukt | Sodium hydride | HCID 24758 | — |
| Edukt | 4-(Chloromethyl)-2-phenyl-1,3-oxazole | HCID 3551196 | — |
| Edukt | Ethyl 3-[1-(4-hydroxybenzyl)-4-phenyl-3-pyrrolyl]propionate | HCID 23024736 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | HCID 23024862 | HCID 23024862 | 72,5% |
Reaktionsschritte
Sodium hydride (60%, oily, 60.0 mg) was added to a solution of ethyl 3-[1-(4-hydroxybenzyl)-4-phenyl-3-pyrrolyl]propionate (524 mg) in N,N-dimethylformamide (10 ml) at 0° C., and the mixture was stirred at room temperature for 15 minutes. 4-Chloromethyl-2-phenyloxazole (290 mg) was added to the mixture, which was stirred at room temperature for 30 minutes. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4), then concentrated. The residue was subjected to silica gel column chromatograpy, and ethyl 3-[4-phenyl-1-[4-(2-phenyl-4-oxazolylmethoxy)benzyl]-3-pyrrolyl]propionate (550 mg, yield: 72%) was obtained as an oily substance from the fraction eluted with ethyl acetate-hexane (1:3, volume ratio).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US07179823B1 |
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| Quelldatensatz | uspto-grants-2007_02 |
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| ORD ID | ord-fba0703fa5e345eab92a22ed95d663ec |
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| Quellennotiz | uspto-grants-2007_02 |
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