Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Sulfoxonium, trimethyl-, iodide (1:1) | HCID 74498 | — |
| Reactant | HCID 59739544 | HCID 59739544 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 59739576 | HCID 59739576 | 28% |
Reaction Steps
Trimethylsulfoxonium iodide (0.28 g, 1.25 mmol) was added to a suspension of sodium hydride (60% by weight in paraffin oil) (0.052 g, 1.3 mmol) in DMSO (4 ml). The mixture was stirred for 30 minutes at room temperature. A solution of 3-[1-(2,6-difluoro-phenyl)-ethenesulfonyl]-5,5-dimethyl-4,5-dihydroisoxazole (prepared according to Example P12) (80% purity) (0.3 g, 0.8 mmol) in DMSO (2 ml) was added dropwise. The mixture was stirred at room temperature for 1 hour. The reaction was quenched by addition of saturated aqueous ammonium chloride solution and the mixture was extracted several times with diethyl ether. The combined organic phases were dried over magnesium sulfate and concentrated. Purification by chromatography on silica gel (eluent: ethyl acetate/hexane) gave the product (Compound No. 1.01 in Table 27) (70 mg, 28% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08680290B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-c25222dddada410792c372f8b504abe6 |
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| Source note | uspto-grants-2014_03 |
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