Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethyl vinyl ether | HCID 8023 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) | HCID 466102 | — |
| Reactant | HCID 67491946 | HCID 67491946 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 68823891 | HCID 68823891 | 19.3% |
Reaction Steps
A mixture of 1 g (4 mmol) of (16) and 0.46 ml (4.8 mmol) ethyl vinyl ether in 2 ml THF was stirred at room temperature in the presence of 201 mg (0.8 mmol) pyridinium p-toluenesulfonate (PPTS) for 4 hours. The mixture was stirred at 40° C. for 2 h and 0.46 ml (4.8 mmol) ethyl vinyl ether were added. After 6 hours at 40° C. the reaction the mixture was hydrolyzed with 3 ml of a saturated aqueous NH4Cl solution. After extraction with 50 ml diethyl ether the combined organic phases were washed (H2O), dried (Na2SO4) and the solvent was evaporated. Flash chromatography, using SiO2 (105 g) and n-pentane/diethyl ether=95:5 as eluent, afforded 215 mg (yield: 19%) of (26).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07470820B2 |
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| Source dataset | uspto-grants-2008_12 |
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| ORD ID | ord-0870dd62ca75406399e14293c593e5b1 |
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| Source note | uspto-grants-2008_12 |
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