Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Phosphoric Acid | HCID 1004 | — |
| Reactant | Trifluoroacetic anhydride | HCID 9845 | — |
| Reactant | Mono-Methyl Succinate | HCID 6930703 | — |
| Reactant | 2-(3-Ethyl-5-methyl-1,2-oxazol-4-yl)-1H-indole | HCID 13038686 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 86740257 | HCID 86740257 | — |
Reaction Steps
A solution of 59.4 grams (0.45 mole) of mono-methyl succinate in 300 ml acetonitrile is treated by dropwise addition with 5.5 grams of 85% phosphoric acid and then by dropwise addition with 63.5 ml (0.45 mole) of trifluoroacetic acid anhydride. The mixture is stirred 15 minutes at room temperature and then treated by dropwise addition with 33.9 grams (0.15 mole) of 2-(3-ethyl-5-methyl-4-isoxazolyl)-indole in 300 ml of acetonitrile. The mixture is stirred at room temperature overnight, after which 1.5 liters of water and 1 liter of ether are added. The two layers are separated, and the ether is washed with water and made basic by the addition of solid sodium carbonate and water. The mixture is stirred 1 hour at room temperature, following which the layers are separated. The ether layer is then washed with water, dried over MgSO4, filtered and evaporated to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04582848 |
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| Source dataset | uspto-grants-1986_04 |
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| ORD ID | ord-058c93c29e0d4114b2dde6412f9c3cef |
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| Source note | uspto-grants-1986_04 |
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