Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Potassium Permanganate | HCID 516875 | — |
| Reactant | Dichloromethane methanol | HCID 21226129 | — |
| Reactant | HCID 44581664 | HCID 44581664 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 9983704 | HCID 9983704 | 72% |
Reaction Steps
The product from Example 144 (0.08 g, 0.18 mmol) was dissolved in 1,4-dioxane (2.0 mL) and KMnO4 (spatula tip) was added. The reaction was heated to 80° C. for 12 h at rt. The reaction was filtered, concentrated, and purified via flash chromatography (silica, 100% EtOAc then 0.5% Et3N:10% MeOH/CH2Cl2 then 100% MeOH) to yield the title compound (0.06 g, yield: 72%). 1H NMR δ 7.44 (d, J=9.1 Hz, 2H), 7.24 (d, J=8.7 Hz, 2H), 6.98 (m, 4H), 4.07 (dd, J=2.9, 3.7 Hz, 2H), 3.81 (s, 3H), 3.48 (s, 2H), 3.12 (t, J=6.2 Hz, 2H), 1.44 (m, 2H), 1.21 (t, J=7.3 Hz, 2H) ppm.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07312214B2 |
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| Source dataset | uspto-grants-2007_12 |
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| ORD ID | ord-361ac7695139419aaf218662d40a857c |
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| Source note | uspto-grants-2007_12 |
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