HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 4-[2-(4-Fluoro-phenyl)-6-methoxy-3-propyl-naphthalen-1-yloxy]-2-trifluoromethyl-benzaldehyde
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 4-Fluoro-2-(trifluoromethyl)benzaldehyde | HCID 522940 | — |
| Reactant | 1,4-Dioxane hydrochloride | HCID 20443148 | — |
| Reactant | 2-(4-Fluoro-phenyl)-6-methoxy-1-methoxymethoxy-3-propyl-naphthalene | HCID 68534652 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | 4-[2-(4-Fluoro-phenyl)-6-methoxy-3-propyl-naphthalen-1-yloxy]-2-trifluoromethyl-benzaldehyde | HCID 86616669 | 98.1% |
Reaction Steps
2-(4-Fluoro-phenyl)-6-methoxy-1-methoxymethoxy-3-propyl-naphthalene (225) (0.6 g, 1.69 mmol), 4 N HCl/Dioxane (12 mL), 4-fluoro-2-trifluoromethyl-benzaldehyde (0.277 mL, 2.03 mmol), Cs2CO3 (1.38 g, 4.23 mmol) and DMSO (12 mL) were reacted as described above to give 0.80 g (98%) of the title compound (226) as oil. 1H NMR (400 MHz, d-CDCl3): δ 0.83 (t, J=7.3 Hz, 3H), 1.47-1.55 (m, 2H), 2.54 (t, J=7.8 Hz, 2H), 3.95 (s, 3H), 6.75 (dd, J=2.3, 8.7 Hz, 1H), 6.94-6.99 (m, 3H), 7.06-7.10 (m, 3H), 7.19 (m, 1H), 7.63-7.66 (m, 2H), 7.89 (d, J=8.8 Hz, 1H), 10.18-10.19 (m, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07649093B2 |
| Source dataset | uspto-grants-2010_01 |
| ORD ID | ord-86a14962cc8140ea83a23dd3b88acaf6 |
| Source note | uspto-grants-2010_01 |