Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrogen Peroxide | HCID 784 | — |
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Brisbenone | HCID 53847321 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86750803 | HCID 86750803 | 88% |
Reaction Steps
A mixture of (5α,25R)-spirost-1-en-3-one (2.87 g, 6.96 mmol), tetrahydrofuran (30 mL), methanol (50 mL) and 15% sodium hydroxide (1 mL) was stirred under nitrogen atmosphere. The mixture was cooled to 0° C. and 30% hydrogen peroxide (5 mL) was added. The reaction mixture was gradually warmed to room temperature and stirred for 4 hours. The reaction was diluted with ethyl acetate, cooled to 0° C., and then quenched with saturated sodium bisulfite solution. The mixture was washed with saturated sodium bisulfite (2×), brine (1×), dried (sodium sulfate), filtered and concentrated in vacuo to give 2.64 g, (88%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05703052 |
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| Source dataset | uspto-grants-1997_12 |
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| ORD ID | ord-cbc90c842c7244a5ba205c2b220bb4b1 |
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| Source note | uspto-grants-1997_12 |
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