Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formic Acid | HCID 284 | — |
| Reactant | 5-Methylfurfural | HCID 12097 | — |
| Reactant | HCID 67352727 | HCID 67352727 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 58392751 | HCID 58392751 | 68.2% |
Reaction Steps
In a closed vessel, a mixture of compound 177 (306 mg, 0.692 mmol), 5-methylfurfural (344 μl, 3.46 mmol), TEA (97 μl, 0.692 mmol) and formic acid (266 μl, 6.92 mmol) in acetonitrile (15 ml) is heated under microwave irradiation for 15 minutes at 140° C. LC-MS shows that the reaction is complete. The solution is partitioned between AcOEt and a saturated solution of NaHCO3, the aqueous phase is extracted with AcOEt and the combined organic layers are washed with brine, dried over Na2SO4 and filtered. The solvent is evaporated to give a oil which is purified by silica gel chromatography (eluent AcOEt/petroleum ether 1/1). Trituration with petroleum ether affords the title compound (236 mg, 0.472 mmol, 68.2% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08481517B2 |
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| Source dataset | uspto-grants-2013_07 |
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| ORD ID | ord-befcc7f4df174944b526489de15e6e53 |
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| Source note | uspto-grants-2013_07 |
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