HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethyl malonate → HCID 67239285, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethyl malonate | HCID 7943 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Methyl 2-(3-bromophenyl)acetate | HCID 11746402 | — |
| Catalyst | Tri-tert-butylphosphine tetrafluoroborate | HCID 2734635 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67239285 | HCID 67239285 | 44.3% |
Reaction Steps
Tris(dibenzylideneacetone)dipalladium(0) (0.104 g, 0.113 mmol), tri-(tert-butyl)phosphonium tetrafluoroborate (65.8 mg, 0.227 mmol) and sodium hydride (295 mg, 60% dispersion in mineral oil) were charged into a flask under an argon atmosphere. (3-Bromophenyl)acetic acid methyl ester (1.30 g, 5.67 mmol) was dissolved in THF (10 ml) and added to the mixture. Subsequently, dimethyl malonate (0.995 g, 7.37 mmol) was added and the mixture stirred under reflux overnight. The mixture was filtered over a small plug of silica gel, evaporated to dryness and the residue purified by silica gel chromatography (HEP/EA gradient) to yield 0.704 g of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09328071B2 |
| Source dataset | uspto-grants-2016_05 |
| ORD ID | ord-6685e20ebfe74a9fa182e79f0c92a14d |
| Source note | uspto-grants-2016_05 |