Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Potassium Acetate | HCID 517044 | — |
| Reactant | HCID 22873910 | HCID 22873910 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 22873905 | HCID 22873905 | 53.3% |
Reaction Steps
A mixture of trifluoromethyl -17β-[3-(4-fluorophenyl )-1-oxopropyl]-androsta-3,5-diene-3-sulfonate (0.28 g, 0.5 mmol), palladium (II) acetate (5.6 mg, 0.025 mmol), triphenylphosphine (13 mg, 0.05 mmol), potassium acetate (0.19 g, 2 mmol) and DMF (6 ml) was heated at 60° C. under an atmosphere of CO for 2.5 hours. The cooled mixture was diluted with ice water, acidified with dilute HCl and extracted with CH2Cl2. The organic extract was washed with water, brine, dried (MgSO4), filtered, concentrated in vacuo, and chromatographed (silica gel, 1% AcOH/19% EtOAc/80% hexanes) to yield the title compound 0.12 g (53%). Recrystallized from methanol-acetone. mp 220°-220° C. analysis for C29H35FO3 0.25 H2O(455.1)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05641765 |
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| Source dataset | uspto-grants-1997_06 |
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| ORD ID | ord-f2b5e0ebd3894fc282b784c1772a1a27 |
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| Source note | uspto-grants-1997_06 |
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