HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Potassium Carbonate → 2-Methyl-5-methylsulfonyl-2,3-dihydro-1-benzofuran
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Potassium Carbonate | HCID 11430 | — |
| Edukt | L-Proline | HCID 145742 | — |
| Edukt | 5-Bromo-2-methyl-2,3-dihydro-1-benzofuran | HCID 13301601 | — |
| Edukt | HCID 178504973 | HCID 178504973 | — |
| Katalysator | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Lösungsmittel | Dimethyl Sulfoxide | HCID 679 | — |
| Produkt | 2-Methyl-5-methylsulfonyl-2,3-dihydro-1-benzofuran | HCID 118022019 | 50% |
Reaktionsschritte
A mixture of 5-bromo-2-methyl-2,3-dihydro-1-benzofuran (1.0 g, 4.72 mmol), CH3SO2Na (730 mg, 7.08 mmol), L-proline (110 mg, 0.94 mmol), K2CO3 (120 mg, 0.94 mmol) and CuI (89 mg, 0.47 mmol) in DMSO (10 mL) was irradiated at 140° C. for 2 h under microwave. The mixture was extracted with EtOAc (2×30 mL). The combined organic layers were washed with brine (30 mL), dried over Na2SO4, filtered and concentrated to give the crude product that was purified by column chromatography on silica gel (PE/EA=2/1) to give the title compound (500 mg, 50%). 1H NMR (CDCl3, 400 MHz) δ 7.71-7.70 (m, 2H), 6.86-6.82 (m, 1H), 5.08-5.03 (m, 1H), 3.41-3.35 (m, 1H), 3.02 (s, 3H), 2.89-2.83 (m, 1H), 1.56 (d, J=6.4 Hz, 3H).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US09034900B2 |
| Quelldatensatz | uspto-grants-2015_05 |
| ORD ID | ord-6ba6bf3a8587433f9f890c0626dc4d42 |
| Quellennotiz | uspto-grants-2015_05 |