HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sulfuric Acid → 3-(3-Cyano-thiophen-2-yl)-3-oxo-propionic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Lithium Bromide | HCID 82050 | — |
| Reactant | 2,2-Bis(trimethylsilyl)propanedioate | HCID 22224580 | — |
| Reactant | 3-Cyanothiophene-2-carbonyl chloride | HCID 22224749 | — |
| Solvent | Isopropenyl acetate | HCID 7916 | — |
| Product | 3-(3-Cyano-thiophen-2-yl)-3-oxo-propionic acid | HCID 22224915 | — |
| Product | 6-(3-Cyano-thiophen-2-yl)-2,2-dimethyl-[1,3]dioxin-4-one | HCID 22224916 | — |
Reaction Steps
The 3-(3-cyano-thiophen-2-yl)-3-oxo-propionic acid was prepared from 3-cyano-thiophene-2-carbonyl chloride (24.33 g, 140.6 mmol) and bis(trimethylsilyl)malonate (38.0 mL, 147.7 mmol) with Et3N (41 mL, 295.4 mmol) and LiBr (13.5 g, 154.7 mmol) in CH3CN at 0° C. according to general procedure H (method c1). The crude material (24.8 g) was transformed into the title compound by stirring in isopropenyl acetate and conc. H2SO4 according to general procedure J (method a). Obtained as an orange solid (5.6 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06509328B1 |
| Source dataset | uspto-grants-2003_01 |
| ORD ID | ord-9c2cb1ca73c84a278aa58e495cd776df |
| Source note | uspto-grants-2003_01 |