HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → HCID 57615034, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Diethyl Malonate | HCID 7761 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 5-Bromo-1-benzothiophene | HCID 2776578 | — |
| Reactant | Tri(tert-butyl)phosphine hexane | HCID 86628723 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 57615034 | HCID 57615034 | 100.6% |
Reaction Steps
To 1,2-dimethoxyethane (10 mL) suspension of 0.02 g of tris(dibenzylideneacetone)dipalladium(0) were added 0.11 g of 10% (w/w) tri(tert-butyl)phosphine/hexane, 1.76 g of cesium carbonate, 0.50 g of 5-bromobenzothiophene and 0.45 g of diethyl malonate, which was then refluxed for 2 hours. To the reaction mixture were added water and ethyl acetate, followed by adjustment to pH2 using 2 mol/L hydrochloric acid. The organic layer was separated, and dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The resultant residue was purified using silica gel column chromatography (eluent; hexane:ethyl acetate=10:1) to provide 0.69 g of diethyl 2-(1-benzothiophen-5-yl)malonate as white solid form.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08273902B2 |
| Source dataset | uspto-grants-2012_09 |
| ORD ID | ord-668dee67ecba4688a987f89563180438 |
| Source note | uspto-grants-2012_09 |