Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Lithium hydroxide, monohydrate | HCID 168937 | — |
| Reactant | HCID 67814343 | HCID 67814343 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 67811908 | HCID 67811908 | 76.2% |
Reaction Steps
To a round bottomed flask was added (4-(2-(4-chlorobenzoyl)phenyl)-3-methylisoxazol-5-yl)methyl benzoate from Example 12 (0.780 g, 1.806 mmol), THF (4 mL), MeOH (4 mL), and water (2 mL). The solution was cooled to 0° C. before addition of lithium hydroxide monohydrate (0.227 g, 5.42 mmol). The reaction was stirred at 0° C. for 45 min before diluting with water and extracting with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford (4-chlorophenyl)(2-(5-(hydroxymethyl)-3-methylisoxazol-4-yl)phenyl)methanone (0.451 g, 1.376 mmol). LC/MS m/z 328 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08796261B2 |
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| Source dataset | uspto-grants-2014_08 |
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| ORD ID | ord-45e815b87fd54b0c867442fa64820bff |
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| Source note | uspto-grants-2014_08 |
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