HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Iodophenol → 1-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-cyclopropanecarbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3-Iodophenol | HCID 12272 | — |
| Reactant | 6-(2-Cyclopentyl-2-hydroxy-4-trimethylsilanyl-but-3-ynyl)-2,2-dimethyl-[1,3]dioxin-4-one | HCID 22499793 | — |
| Reactant | 1-(4-Bromo-2-fluorophenyl)cyclopropane-1-carbonitrile | HCID 58762329 | — |
| Product | 1-{4-[3-Cyclopentyl-4-(2,2-dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-3-hydroxy-but-1-ynyl]-2-fluoro-phenyl}-cyclopropanecarbonitrile | HCID 58762334 | — |
Reaction Steps
The desired product was prepared analogously to example F(7), tep 5, substituting 1-(4-bromo-2-fluoro-phenyl)-cyclopropanecarbonitrile (0.96 g, 4.0 mmol), from Step 2 above in place of 3-iodophenol, and 6-(2-cyclopentyl-2-hydroxy-but-3-ynyl)-2,2-dimethyl-[1,3]dioxin-4-one (1.06 g, 4.0 mmol; from Step 4 above) in place of 6-but-3-ynyl-3-chloro-6-cyclopentyl-dihydro-pyran-2,4-dione. Yield: 1.241 g, 73%. MS (ESI): 422 (M−H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07473790B2 |
| Source dataset | uspto-grants-2009_01 |
| ORD ID | ord-f257a02736124e81ae034122e4e8829c |
| Source note | uspto-grants-2009_01 |