HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cyclohexanol → HCID 24698739, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cyclohexanol | HCID 7966 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Sodium bis(trimethylsilyl)amide | HCID 2724254 | — |
| Reactant | 6-Chloro-3-pyridinecarbonitrile | HCID 5152094 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 24698739 | HCID 24698739 | 71.4% |
Reaction Steps
Add sodium bis(trimethylsilyl)amide (3.9 mL, 7.93 mmol, 2M solution in THF) to a solution of cyclohexanol (824 μL, 7.93 mmol) in THF (10 mL). Stir for 30 min at room temperature and then add a solution of 6-chloro-nicotinonitrile (1 g, 7.2 mmol) in anhydrous THF (5 mL). Stir at room temperature overnight and then quench the reaction by addition of saturated aqueous NaHCO3 (100 mL) and extract the aqueous phase with DCM (3×100 mL). Wash the combined organic extracts with brine (100 mL), dry over MgSO4 and concentrate in vacuo to obtain the desired intermediate as a yellow solid (1.04 g, 71%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08680091B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-1737371c591e4d83b152affbe583b73f |
| Source note | uspto-grants-2014_03 |