Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrofluoric Acid | HCID 14917 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 70981482 | HCID 70981482 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86714670 | HCID 86714670 | — |
Reaction Steps
Ethyl 3-(1-((tert-butyldiphenylsilyl)oxy)ethyl)-1,2,4-oxadiazole-5-carboxylate (5.90 mmol, 2.5 g) was dissolved in THF and cooled to 0° C. with an ice bath. 70% Hydrogen fluoride in pyridine (1.5 ml) was added slowly. After addition, the reaction mixture was stirred at ambient temperature for overnight. The reaction mixture was basified by aqueous NaHCO3 solution and extracted with DCM. The organic layers were washed with water, dried, filtered and evaporated. The product was purified by flash-chromatography. Yield 897 mg. 1H-NMR (400 MHz; CDCl3): δ 1.46 (t, 3H), 1.66 (d, 3H), 4.53 (q, 2H), 5.11 (q, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08921378B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-fc6f0bb745c4447ea61c349828ae88ac |
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| Source note | uspto-grants-2014_12 |
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