HuagongsheHuagongshe Chemistry Print Report · For research reference only
1H-Isoindole-1,3(2H)-dione, 2-(bromomethyl)- → Methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(thiophen-3-yl)propanoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1H-Isoindole-1,3(2H)-dione, 2-(bromomethyl)- | HCID 79244 | — |
| Reactant | Methyl 3-thienylacetate | HCID 94041 | — |
| Reactant | Lithium Hexamethyldisilazide | HCID 2733832 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(thiophen-3-yl)propanoate | HCID 59161752 | — |
Reaction Conditions
| Temperature | -78 °C |
|---|
Reaction Steps
To pure methyl 2-(thiophen-3-yl)acetate in THF cooled to −78° C. was added LiHMDS and the solution stirred at −78° C. for 30 min. Then N-(bromomethyl)phthalimide was added directly and the solution was allowed to warm to 0° C. The mixture was poured into NaHCO3(sat) extracted with EtOAc, dried (Na2SO4), filtered, and evaporated. Column chromatography (SiO2, 0-40% EtOAc/Hex) gave pure methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(thiophen-3-yl)propanoate (E429).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08716310B2 |
| Source dataset | uspto-grants-2014_05 |
| ORD ID | ord-0d4496892afc4f7782539dbb188f9521 |
| Source note | uspto-grants-2014_05 |