HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 3-(2,2-Dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-benzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | 3-Cyanobenzoyl chloride | HCID 308483 | — |
| Reactant | 2,2-Bis(trimethylsilyl)propanedioate | HCID 22224580 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Isopropenyl acetate | HCID 7916 | — |
| Product | 3-(2,2-Dimethyl-6-oxo-6H-[1,3]dioxin-4-yl)-benzonitrile | HCID 11736337 | — |
| Product | 3-(3-Cyano-phenyl)-3-oxo-propionic acid | HCID 22224560 | — |
Reaction Steps
The 3-(3-cyano-phenyl)-3-oxo-propionic acid was prepared from 3-cyanobenzoyl chloride (828 mg, 5 mmol) and bis(trimethylsilyl)malonate (2.56 mL, 10 mmol) with n-BuLi (1.6M in hexane, 6.25 mL) in ether at −60° C. to 0° C. according to general procedure H (method c2). The crude material (1.04 g) was transformed into the title compound by stirring in isopropenyl acetate and TFA according to general procedure J (method a). Obtained as a light yellow solid (0.8 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07151098B2 |
| Source dataset | uspto-grants-2006_12 |
| ORD ID | ord-6bb19336f5d24d2b93e1d1e4aa7c53af |
| Source note | uspto-grants-2006_12 |