Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Potassium bis(trimethylsilyl)amide | HCID 3251421 | — |
| Reactant | HCID 18459233 | HCID 18459233 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 18459230 | HCID 18459230 | 82% |
Reaction Steps
To a solution potassium bis(trimethylsilyl)amide (0.213 g, 1.068 mmol) in tetrahydrofuran (1 ml) at −78° C. was added (±)-diethyl 3-ethoxycarbonyl-5-(4-(octyl)phenyl)pentylphosphonate (0.250 g, 0.533 mmol) as a solution in 1 ml of tetrahydrofuran. After stirring for 40 minutes at −78° C., iodomethane (0.083 ml, 1.33 mmol) was added. The reaction was stirred for 1 h at −78° C. then allowed to warm to room temperature. The solution was diluted with ethyl acetate (25 ml) and washed with 2N HCl (10 ml) 5% aqueous sodium thiosulfate (10 ml), saturated aqueous sodium chloride (10 ml), dried over magnesium sulfate and concentrated to give a colorless oil (0.211 g): MS m/e 483.4 (M+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06437165B1 |
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| Source dataset | uspto-grants-2002_08 |
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| ORD ID | ord-c9bca06bbccd455f912325d2479ef974 |
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| Source note | uspto-grants-2002_08 |
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