HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 1-(4-methyl-thiazol-2-yl)-cyclopropanecarboxylic Acid Ethyl Ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 1,2-Dibromoethane | HCID 7839 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Ethyl 2-(4-methyl-1,3-thiazol-2-yl)acetate | HCID 574575 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 1-(4-methyl-thiazol-2-yl)-cyclopropanecarboxylic Acid Ethyl Ester | HCID 66770932 | 99.9% |
Reaction Steps
Ethyl 2-(4-methylthiazol-2-yl)acetate (1 g, 5.4 mmol, Eq: 1.00) was dissolved in DMF (5 mL). 1,2-dibromoethane (1.62 g, 744 μL, 8.64 mmol, Eq: 1.60) and Cs2CO3 (4.4 g, 13.5 mmol, Eq: 2.50) were added. The reaction mixture was stirred 48 h at RT. The reaction mixture was poured into 0.5 M aqueous HCl (100 mL) and extracted with EtOAc (3×50 mL). The combined organic layers were dried over Na2SO4, filtered and evaporated. The crude material was purified by flash chromatography (silica gel, 50 g, 0% to 50% EtOAc in heptane) to yield 1.14 g (73.6%) of a light yellow liquid. MS (ESI): m/z=212.0 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08163793B2 |
| Source dataset | uspto-grants-2012_04 |
| ORD ID | ord-8f4ea559448f47c8bbc435385e9194b6 |
| Source note | uspto-grants-2012_04 |