HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trifluoroacetic acid → 3-Oxo-3-thiophen-2-yl-propionic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | 2-Thiophenecarbonyl chloride | HCID 78928 | — |
| Reactant | 2,2-Bis(trimethylsilyl)propanedioate | HCID 22224580 | — |
| Reactant | Butyllithium | HCID 178418339 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Isopropenyl acetate | HCID 7916 | — |
| Product | 3-Oxo-3-thiophen-2-yl-propionic acid | HCID 12604610 | — |
| Product | 2,2-Dimethyl-6-thiophen-2-yl-[1,3]dioxin-4-one | HCID 22224708 | — |
Reaction Steps
The 3-oxo-3-thiophen-2-yl-propionic acid was prepared from thiophene-2-carbonyl chloride (5.3 mL, 50 mmol) and bis(trimethylsilyl)malonate (25.6 mL, 100 mmol) with n-BuLi (1.6M in hexane, 62.5 mL) in ether at −60° C. to 0° C. according to the general procedure H (method c2). The crude material (7.88 g) was transformed into the title compound by stirring in isopropenyl acetate and TFA according to the general procedure J (method a). Obtained as a yellow solid (4.09 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06509328B1 |
| Source dataset | uspto-grants-2003_01 |
| ORD ID | ord-3f9476071c9b4a939067ec14956b5dfc |
| Source note | uspto-grants-2003_01 |