Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | Lithium diisopropylamide | HCID 2724682 | — |
| Reactant | HCID 14774099 | HCID 14774099 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 15075812 | HCID 15075812 | 90.6% |
Reaction Steps
A solution of 0.64 mL (4.57 mmol) of diisopropylamine in 20 mL of dry THF under argon was cooled to -78° C. and treated with 2.1 mL (4.20 mmol) of 2.0N n-butyllithium. The LDA solution was stirred at -78° C. for 15 minutes, then warmed to 0° C. To this solution was added a solution of 1.05 g (3.5 mmol) of 2-(2,4,5- trifluoro-3-trimethylsilylphenyl)-4,4-dimethyl-2-oxazoline in 5 mL of THF; the reaction mixture was stirred at 0° C. for 45 minutes, then quenched with 1.50 g (10.6 mmol) of methyl iodide. The solution was stirred at room temperature for 3 hours and diluted with water. The organic layer was washed with water, dried over magnesium sulfate, and concentrated to give 1.00 g of the title compound as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05585491 |
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| Source dataset | uspto-grants-1996_12 |
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| ORD ID | ord-f3cfe5a9a3194d169a4ed897249b671a |
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| Source note | uspto-grants-1996_12 |
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