Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1-Dibromoethane | HCID 11201 | — |
| Reactant | 6-Methoxy-2-naphthol | HCID 288634 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 17984322 | HCID 17984322 | 30.1% |
Reaction Steps
To a solution of 6-methoxynaphthalen-2-ol (1.07 g, 6.14 mmol) in DMF (4 mL) were added cesium carbonate (3.11 g, 9.55 mmol) and dibromoethane (2.5 mL, 29 mmol). The mixture was stirred and heated at 55° C. for 48 h. The reaction mixture was cooled, filtered, diluted with EtOAc, and washed with brine (2×30 mL). The organic layer was dried (Na2SO4) and concentrated. The crude product was purified using radial chromatography (2:98 to 25:75 EtOAc:Hex) to give the title compound as a white solid (0.52 g, 30%): 1H NMR (400 MHz, CDCl3) δ 3.61 (t, J=6.1 Hz, 2H), 3.82 (s, 3H), 4.30 (t, J=6.4 Hz, 2H), 7.01-7.08 (m, 4H), 7.56 (dd, J=12.0, 9.0 Hz, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07282501B2 |
|---|
| Source dataset | uspto-grants-2007_10 |
|---|
| ORD ID | ord-d3ff1e5e7d0e4f82aceb889b0b49e77e |
|---|
| Source note | uspto-grants-2007_10 |
|---|