Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 2,2,2-Trifluoroethanol | HCID 6409 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 19837307 | HCID 19837307 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 14769997 | HCID 14769997 | 57% |
Reaction Steps
In a stream of nitrogen, 2.0 ml of 2,2,2-trifluoroethanol was added to 52.8 mg of sodium hydride, and then a solution of 140 mg of copper iodide and 922 mg of 4-(4-bromobenzyl)pyridine in 4 ml of N,N'-dimethylformamide was added. The mixture was stirred at a bath temperature of 120° C. for 3 hours. After the reaction, water was added to the reaction mixture, and it was extracted with ethyl acetate. The extract was washed with water, and the solvent was evaporated. 0.78 g of the residue was distilled under reduced pressure by using a Kugel-Rohr. When 574 mg (yield 57%) of a fraction having a boiling point of 150° C. (0.2 mmHg) was separated, 4-[4-(2,2,2-trifluoroethoxy)benzyl]pyridine was obtained as colorless crystals having a melting point of 51° to 53° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04886822 |
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| Source dataset | uspto-grants-1989_12 |
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| ORD ID | ord-039eee98b8224f49b3c3ceac1c0b23d6 |
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| Source note | uspto-grants-1989_12 |
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