HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 5-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-methylthiophene-2-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Dicyclohexylcarbodiimide | HCID 10868 | — |
| Reactant | Hydroxyamine hydrochloride | HCID 443297 | — |
| Reactant | 5-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-methylthiophene-2-carboxaldehyde | HCID 86620221 | — |
| Product | 5-({[t-Butyl(dimethyl)silyl]oxy}methyl)-3-methylthiophene-2-carbonitrile | HCID 68528449 | — |
Reaction Steps
The crude product of the title compound was synthesized by conducting the reaction similar to that mentioned in Example 10 (10c) using 5-({[t-butyl(dimethyl)silyl]oxy}methyl)-3-methylthiophene-2-carboxaldehyde (2.5 g, 9.2 mmol) that was obtained in Example 11 (11b), hydroxylamine hydrochloride (0.71 g, 10 mmol), triethylamine (2.6 mL, 18 mmol), and N,N′-dicyclohexylcarbodiimide (2.1 g, 10 mmol). Subsequently, the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (0:10 to 5:95) as the eluent to afford the title compound (2.5 g) in a yield of 100% as a pale yellowish oily product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07687491B2 |
| Source dataset | uspto-grants-2010_03 |
| ORD ID | ord-51485fbdc89d47dcb6de507a8977477b |
| Source note | uspto-grants-2010_03 |