Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|
| Edukt | Cesium carbonate | HCID 10796 | — |
| Edukt | Benzene, 1-iodo-3-methoxy- | HCID 69839 | — |
| Edukt | 5-Methyl-1,10-phenanthroline | HCID 72791 | — |
| Edukt | 1-Phenylethanol, (R)- | HCID 637516 | — |
| Katalysator | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Lösungsmittel | Toluene | HCID 1140 | — |
| Produkt | HCID 11310736 | HCID 11310736 | 76% |
Reaktionsschritte
A test tube was charged with CuI (20 mg, 0.10 mmol, 10 mol %), 5-methyl-1,10-phenanthroline (39 mg, 0.20 mmol, 20 mol %), Cs2CO3 (652 mg, 2.0 mmol), 3-iodoanisole (119 μL, 1.0 mmol), (R)-(+)-1-phenylethanol (205 μL, 1.7 mmol, >99% ee) and toluene (1 mL). The test tube was sealed and the reaction mixture was stirred at 110° C. for 32 h. The resulting suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel eluting with ethyl acetate. The filtrate was concentrated. Purification of the residue by flash chromatography on silica gel (2×20 cm; hexane/ethyl acetate 30:1) provided 173 mg (76% yield, 98% ee) of the title compound as a colorless oil.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patentnummer | US06867298B2 |
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| Quelldatensatz | uspto-grants-2005_03 |
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| ORD ID | ord-5f727b1700d045d6bf915b5fe38d84bd |
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| Quellennotiz | uspto-grants-2005_03 |
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