HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetic Acid → C29H28ClNO2
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetic Acid | HCID 176 | — |
| Reactant | 2-[3-(S)-[3-(2-(7-Chloro-2-quinolinyl)(E/Z)ethenyl)phenyl]-3-hydroxypropyl]benzoic acid methyl ester | HCID 54006303 | — |
| Reactant | HCID 178418689 | HCID 178418689 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Tetrahydrofuran toluene | HCID 22635083 | — |
| Product | C29H28ClNO2 | HCID 54563620 | — |
Reaction Steps
To a solution of the hydroxyester of Step 2 (38.68 g, 84.36 mmol) in 600 mL of toluene at 0° C. was added slowly 225 mL of 1.5M MeMgBr in toluene:THF 3:1 and the mixture was stirred at r.t. for 4 h. It was then poured into 2 L cold 12% NH4OAc and 25 mL of AcOH were added. The products were extracted in EtOAc, washed with brine, dried over Na2SO4 and concentrated. Flash chromatography of the residue with EtOAc:toluene 15:85 and 25:75 afforded first the methyl ketone derivative, then the title compound. Yield 24.06 g, 62%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05565473 |
| Source dataset | uspto-grants-1996_10 |
| ORD ID | ord-29f4a3ddf35c4330983b282c96d0ef52 |
| Source note | uspto-grants-1996_10 |