HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 4-(2-Cyclopropylethoxy)-4-(4-fluorophenyl)-1-phenylcyclohexanecarbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | (2-Bromoethyl)cyclopropane | HCID 22636989 | — |
| Reactant | 4-(4-Fluorophenyl)-4-hydroxy-1-phenylcyclohexanecarbonitrile | HCID 59442573 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 4-(2-Cyclopropylethoxy)-4-(4-fluorophenyl)-1-phenylcyclohexanecarbonitrile | HCID 59442511 | 47.1% |
Reaction Steps
500 mg of the compound of Example 1, 760 mg of (2-bromoethyl)cyclopropane (Chorvat et al., J. Med. Chem. 28, 194-200 (1985)) and 122 mg of sodium hydride in 20 ml of anhydrous DMF were stirred at room temperature for 19 h. 760 mg of (2-bromoethyl)cyclopropane and 122 mg of sodium hydride were then added and the mixture was stirred at room temperature for 4 days. The reaction mixture was then treated with 100 ml of water and extracted three times with 50 ml each of EA. The combined organic phases were dried over magnesium sulfate and the solvent was removed in vacuo. 290 mg of the title compound were obtained as a pale yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08076324B2 |
| Source dataset | uspto-grants-2011_12 |
| ORD ID | ord-f6ffb8353fe14f5891972cf2c9430c43 |
| Source note | uspto-grants-2011_12 |