HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → [2-Fluoro-4-(8-hydroxy-2,2,4,4-tetramethyl-chroman-6-ylethynyl)phenyl]-acetic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 2-Fluoro-4-iodo phenyl acetic acid methyl ester | HCID 18710225 | — |
| Reactant | 6-Ethynyl-8-hydroxy-2,2,4,4-tetramethyl-chroman | HCID 21107228 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Hexane | HCID 8058 | — |
| Product | [2-Fluoro-4-(8-hydroxy-2,2,4,4-tetramethyl-chroman-6-ylethynyl)phenyl]-acetic acid methyl ester | HCID 69075483 | — |
Reaction Steps
Following General Procedure B and using 6-ethynyl-8-hydroxy-2,2,4,4-tetramethyl-chroman (Intermediate 19, 0.05 g, 0.22 mmol), 2-fluoro-4-iodo phenyl acetic acid methyl ester (0.096 g, 0.33 mmol), triethyl amine (3 mL), copper(I)iodide (0.020 g, 0.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.07 g, 0.1 mmol) followed by flash column chromatography over silica gel (230-400 mesh), and preparative normal phase HPLC using 10% ethyl acetate in hexane as the mobile phase, the title compound was obtained (0.037 g, 43%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07638648B2 |
| Source dataset | uspto-grants-2009_12 |
| ORD ID | ord-0c3c29d958fe44f98694eb8dc863df02 |
| Source note | uspto-grants-2009_12 |