Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | HCID 67040741 | HCID 67040741 | — |
| Catalyst | Iron | HCID 23925 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 67040515 | HCID 67040515 | 74% |
Reaction Steps
The product of Example 231C (146.5 mg, 0.2195 mmol), ammonium chloride (77 mg, 1.438 mmol), and iron powder (75.4 mg, 1.35 mmol) in a mixture of water (3 mL), ethanol (6 mL) and tetrahydrofuran (6 mL) was heated at 80° C. under a nitrogen atmosphere for 1 hour. The reaction was cooled to room temperature, diluted with ethyl acetate (100 mL), and washed with water (3×50 mL) and brine (50 mL). The organic was dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation in vacuo. Purification by silica gel chromatography eluting with 4% methanol/methylene chloride afforded the title compound as a yellow solid (103 mg, 74%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07910595B2 |
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| Source dataset | uspto-grants-2011_03 |
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| ORD ID | ord-6dc64644cc934e5d8c78bc53d3c61d0f |
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| Source note | uspto-grants-2011_03 |
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