Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Diisopropylamine | HCID 7912 | — |
| Reactant | HCID 9728 | HCID 9728 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | 1,3-dithiane-2-carbonitrile | HCID 311839 | — |
| Reactant | Lithium diisopropylamide | HCID 2724682 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 53760192 | HCID 53760192 | — |
Reaction Steps
A solution of 1.45 g (10 mMole) of 1,3-dithian-2-carbonitrile in 10 ml of tetrahydrofuran is added to lithium diisopropylamide, prepared from diisopropylamine (1.01 g, 10 mMole) and butyllithium (4.8 ml of a 2.1 M solution, 10 mM) in 20 ml of tetrahydrofuran at -70° C. To the solution is added 1.25 g (9,5 mMole) of 3-monofluoromethylacrylic acid ethyl ester in 5 ml of tetrahydrofuran and the reaction mixture is stirredat -70° C. for 30 minutes after which 1.3 g (10 mMole) of methyl iodide is added and the mixture is maintained at 0° C. for 15 hours, then poured into aqueous ammonium chloride and extracted with ether. The ether solution is dried and evaporated to give the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04277395 |
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| Source dataset | uspto-grants-1981_07 |
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| ORD ID | ord-4111cf2876f04d50b243b775774c20af |
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| Source note | uspto-grants-1981_07 |
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