Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Thiophene, 2-(1-azidoethyl)-5-fluoro- | HCID 86602490 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 54329319 | HCID 54329319 | 73.7% |
Reaction Steps
Triphenylphosphine (873 mg) was added to a solution of 2-(1-azidoethyl)-5-fluorothiophene (518 mg) in THF (10 mL), and the reaction solution was stirred at room temperature for 1 hour. Water (2 mL) was added to the reaction mixture, and the mixture was heated to reflux for 3 hours. After allowing the reaction mixture to be cooled, a 5 N aqueous solution of hydrochloric acid and ethyl acetate were added thereto to separate the aqueous layer. A 5 N aqueous solution of sodium hydroxide was added to the aqueous layer to make the layer basic, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 324 mg of the title compound. The physical properties of the compound are as follows.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07880009B2 |
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| Source dataset | uspto-grants-2011_02 |
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| ORD ID | ord-f2f8e2464a324152abc7a980f89c40a5 |
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| Source note | uspto-grants-2011_02 |
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