Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Acrylonitrile | HCID 7855 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | 2-(1-Benzothiophen-5-yl)ethan-1-ol | HCID 11983371 | — |
| Catalyst | Tetrabutylammonium Bromide | HCID 74236 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 21990147 | HCID 21990147 | — |
Reaction Steps
To 2.00 g of 2-(1-benzothiophen-5-yl)-1-ethanol were added 13 mg of potassium hydroxide, 36 mg of tetra-n-butylammonium bromide and 1.11 mL of acrylonitrile, and the resulting mixture was stirred at 45° C. for 3 hours. After the reaction mixture was cooled, water and ethyl acetate were added thereto and the pH was adjusted to 1 with 2 mol/L hydrochloric acid. The insoluble materials were removed and then the organic layer was separated. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a column chromatography (eluent; hexane:ethyl acetate=3:1) to obtain 2.46 g of 3-[2-(1-benzothiophen-5-yl)ethoxy]propiono-nitrile as a colorless oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07468443B2 |
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| Source dataset | uspto-grants-2008_12 |
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| ORD ID | ord-0095d39e4fdb429cb8e598fe4bf98d78 |
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| Source note | uspto-grants-2008_12 |
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