HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sulfuric Acid → 3-(3-Chloro-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 | 3-Chlorothiophene-2-carbonyl chloride | HCID 2735824 | — |
| Reactant | 2,2-Bis(trimethylsilyl)propanedioate | HCID 22224580 | — |
| Solvent | Isopropenyl acetate | HCID 7916 | — |
| Product | 3-(3-Chloro-thiophen-2-yl)-3-oxo-propionic acid | HCID 22224616 | — |
| Product | 6-(3-Chloro-thiophen-2-yl)-2,2-dimethyl-[1,3]dioxin-4-one | HCID 22224775 | — |
Reaction Steps
The 3-(3-chloro-thiophen-2-yl)-3-oxo-propionic acid was prepared from 3-chloro-thiophene-2-carbonyl chloride (7.82 g, 43.2 mmol) and bis(trimethylsilyl)malonate (11.6 mL, 45.4 mmol) with Et3N (12.65 mL, 90.7 mmol) and LiBr (3.53 g, 47.5 mmol) in CH3CN at 0° C. according to general procedure H (method c1). The crude material (5.69 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 (2.3 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06960578B2 |
| Source dataset | uspto-grants-2005_11 |
| ORD ID | ord-2671be551f05412d8a90afb5f399ffd7 |
| Source note | uspto-grants-2005_11 |