Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | HCID 67168642 | HCID 67168642 | — |
| Reactant | Jones' reagent | HCID 131709961 | — |
| Solvent | Acetone | HCID 180 | — |
| Product | HCID 67170130 | HCID 67170130 | 93% |
Reaction Steps
Ethyl 5-(2-hydroxypropyl)isoxazole-3-carboxylate (1.5 g, 7.53 mmol) was dissolved in acetone (40 ml) and cooled to 0° C. Jones' reagent (5.90 ml, 7.91 mmol) was added dropwise and the reaction mixture was stirred at 0 C for 30 min. Then the reaction mixture was allowed to warm up to RT and stirred 18 h. Mixture of methanol (30 ml) and water (30 ml) was added and then the volatiles were evaporated. The residue was extracted with DCM, dried with Na2SO4 and evaporated to dryness to afford 1.38 g (93%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): 6, 1.32 (t, 3H), 2.22 (s, 3H), 4.29-4.44 (m, 2H), 4.22 (s, 2H), 6.67 (s, 1H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08975254B2 |
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| Source dataset | uspto-grants-2015_03 |
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| ORD ID | ord-dad9accdc9b849ee8b5bf9697291b985 |
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| Source note | uspto-grants-2015_03 |
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