HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dimethoxyethane → HCID 68516153, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dimethoxyethane | HCID 8071 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 3-Fluorophenylboronic acid | HCID 2733986 | — |
| Reactant | Methyl 5-bromo-2-methylfuran-3-carboxylate | HCID 15534190 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 68516153 | HCID 68516153 | 92% |
Reaction Steps
A mixture of methyl 5-bromo-2-methyl-3-furancarboxylate (2.2 g), 3-fluorophenylboronic acid (1.7 g), tetrakis(triphenylphosphine)palladium(0) (0.6 g), 2N aqueous sodium carbonate solution (12 mL) and 1,2-dimethoxyethane (20 mL) was stirred overnight with refluxing under an argon atmosphere. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (0% ethyl acetate/hexane to 15% ethyl acetate/hexane), and crystallized from ethyl acetate/hexane to give the title compound (2.1 g, 92%) as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08309580B2 |
| Source dataset | uspto-grants-2012_11 |
| ORD ID | ord-87af462716a64c3d946e8f616556d75f |
| Source note | uspto-grants-2012_11 |