HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl iodide → Methyl 2-(2,2-dimethyl-1-(methyloxy)butyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl iodide | HCID 6328 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Methyl 2'-fluoro-2-(1-hydroxy-2,2-dimethylbutyl)-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate | HCID 57706901 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Methyl 2-(2,2-dimethyl-1-(methyloxy)butyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate | HCID 57706189 | 64% |
Reaction Steps
To a solution of 66.62A (0.39 g, 1.1 mmol) in DMF (5 mL), was added NaH (0.034 g, 1.4 mmol). The mixture was stirred at room temperature for 10 minutes and then iodomethane (0.20 mL, 3.2 mmol) was added. The mixture was stirred at room temperature for 60 minutes and then it was diluted with EtOAc, washed with water and brine, and dried over anhydrous Na2SO4. After removing solvent, the residue was purified by flash chromatography (silica gel, 1:9 EtOAc/hexane) and gave 66.62B, colorless oil, in 64% yield (260 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08030354B2 |
| Source dataset | uspto-grants-2011_10 |
| ORD ID | ord-3cdb046a326d4194965b5649aff67847 |
| Source note | uspto-grants-2011_10 |