Cyclopentylacetylene → Methyl 4-(cyclopentylethynyl)-2-methylbenzoate

HRID 2102918

Reaktionsgleichung

Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[CH:3]=1.[C:13]([CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)#[CH:14]>C(N(CC)CC)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:15]1([C:13]#[C:14][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([CH3:12])[CH:3]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

Methyl 4-bromo-2-methylbenzoate (1.0 g, 4.4 mmol) was dissolved in triethylamine (5 mL). To the mixture was added copper iodide (43 mg, 5 mol %), followed by PdCl2(PPh3)2 (157 mg, 5 mol %) and ethynylcyclopentane (0.75 mL, 5.3 mmol). The mixture was heated in a sealed pressure tube at 80° C. for 3 hours. After completion of the reaction, the triethylamine was evaporated and the residue was dissolved in EtOAc and filtered through Celite®. The organic layer was washed with water, brine, and dried (Na2SO4), then filtered and concentrated under vacuum. The residue was purified by column chromatography on sililca gel using EtOAc-hexane (0-100% gradient) as eluet to give the desired product.

Aufarbeitung

customAfter completion of the reaction
customthe triethylamine was evaporated
dissolutionthe residue was dissolved in EtOAc
filtrationfiltered through Celite®
washThe organic layer was washed with water, brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated under vacuum
customThe residue was purified by column chromatography on sililca gel

Quellen und Nachweise

ORD-Eintrag: ord-5857646d2e6a4d60b7c85b4128a7d606
Quelldatensatz: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07576099B2

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