HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → 4-(Tert-butyl-dimethylsilyloxyethyl)-2-cyanopyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Trimethylsilyl cyanide | HCID 82115 | — |
| Reactant | 4-(2-{[tert-Butyl(dimethyl)silyl]oxy}ethyl)-1-oxo-1lambda~5~-pyridine | HCID 19757789 | — |
| Solvent | Hexane | HCID 8058 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | 4-(Tert-butyl-dimethylsilyloxyethyl)-2-cyanopyridine | HCID 22321709 | — |
Reaction Steps
A solution of 28.6 g of 4-(tert-butyl-dimethylsilyloxyethyl)-pyridine-N-oxide, 60.3 ml of trimethylsilyl cyanide and 31.5 ml triethylamine is stirred under nitrogen at reflux for 3 hours. The dark solution is cooled in an ice bath, 30 ml of ethanol added, followed by 400 ml ethyl acetate and 200 ml hexane. The solution is washed twice with 150 ml of water, dried over sodium sulfate, filtered, concentrated in vacuo and purified by flash chromatography using ethyl acetate/hexane (1:10) to yield 4-(tert-butyl-dimethylsilyloxyethyl)-2-cyanopyridine.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04906621 |
| Source dataset | uspto-grants-1990_03 |
| ORD ID | ord-ef3251110d9140bbb2ee4459118cd22f |
| Source note | uspto-grants-1990_03 |