Tetrahydrofuran → Tris(4-ethynylphenyl)amine

HRID 1840695Notizen

Reaktionsgleichung

O1CCCC1.C[Si]([C:10]#[C:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]([C:31]2[CH:36]=[CH:35][C:34]([C:37]#[C:38][Si](C)(C)C)=[CH:33][CH:32]=2)[C:19]2[CH:24]=[CH:23][C:22]([C:25]#[C:26][Si](C)(C)C)=[CH:21][CH:20]=2)=[CH:14][CH:13]=1)(C)C.[F-].[K+]>CO>[C:25]([C:22]1[CH:21]=[CH:20][C:19]([N:18]([C:15]2[CH:14]=[CH:13][C:12]([C:11]#[CH:10])=[CH:17][CH:16]=2)[C:31]2[CH:36]=[CH:35][C:34]([C:37]#[CH:38])=[CH:33][CH:32]=2)=[CH:24][CH:23]=1)#[CH:26]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a mixture of 180 ml of tetrahydrofuran (THF) and 240 ml of methanol were added 13.84 g (0.026 mol) of tri(4-trimethylsilylethynylphenyl)amine and 4.53 g (0.078 mol) of potassium fluoride. The reaction mixture was heated at 50° C. for 5 h, cooled down to room temperature, and solvent was removed under the reduced pressure. The residue was extracted with ether and the ether layer was washed with distilled water. The washed ether layer was concentrated to give crude product. The crude product was purified by column chromatography on silica gel by eluting with hexane to give 6.182 g (75%) of tri(4-ethynylphenyl)amine of which NMR spectrum was shown in FIG. 9 and mp was 115° C.

Aufarbeitung

temperaturecooled down to room temperature
customsolvent was removed under the reduced pressure
extractionThe residue was extracted with ether
washthe ether layer was washed with distilled water
concentrationThe washed ether layer was concentrated
customto give crude product
customThe crude product was purified by column chromatography on silica gel
washby eluting with hexane

Quellen und Nachweise

ORD-Eintrag: ord-571735d7247149858c6a591f017d96ed
Quelldatensatz: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06682782B2

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