HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → HCID 11850964, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Potassium Trifluoro(methyl)borate | HCID 23692566 | — |
| Reactant | HCID 59218523 | HCID 59218523 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 11850964 | HCID 11850964 | — |
Reaction Steps
The ester is formed according to the method of Molander et al. (J. Org. Chem. 68, 5534, (2003)). To a stirring suspension of potassium methyltrifluoroborate (629.0 mg, 5.2 mmol) Cs2CO3 (5.0 g, 15.5 mmol), PdCl2(dppf).CH2Cl2 (46.0 mg, 0.057 mmol), and triflate (46.3) (2.0 g, 5.7 mmol) in 50 mL THF is added water (5 mL) under an argon atmosphere. Stirring the mixture at reflux until TLC confirms the consumption of the starting material. The mixture is cooled to room temperature, and is diluted with water and extracted with ether. The combined organic layers are dried (MgSO4) and concentrated under reduced pressure. The residue is purified by column chromatography (silica, EtOAc/Hexane), to afford ester 46.4.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07687526B2 |
| Source dataset | uspto-grants-2010_03 |
| ORD ID | ord-238fd8ff245c44fbbf13510e519f22cb |
| Source note | uspto-grants-2010_03 |