Tetrabutylammonium Fluoride → (4-Tert-butyl-benzyl)-[2-(3-ethynyl-phenyl)-ethyl]-carbamic acid tert-butyl ester

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Reaktionsgleichung

[C:1]([O:5][C:6](=[O:33])[N:7]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[C:17][Si](C)(C)C)[CH:11]=1)([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.[Cl-].[Na+].O>[C:1]([O:5][C:6](=[O:33])[N:7]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([CH3:32])([CH3:31])[CH3:30])=[CH:25][CH:24]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[CH:17])[CH:11]=1)([CH3:3])([CH3:4])[CH3:2]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of (4-tert-butyl-benzyl)-[2-(3-trimethylsilanylethynyl-phenyl)-ethyl]-carbamic acid tert-butyl ester (440 mg, 0.949 mmol) in THF (7.6 ml) was added a 1 molar solution of TBAF in THF (949 μl, 0.949 mmol) at −78° C. After 15 min at −78° C. the solution was allowed to warm to 0° C. for 30 min. Then brine was added and the mixture was extracted with ether. The combined ether layers were dried (Na2SO4) and evaporated and the remaining residue was purified by chromatography (pentane/ether 100:0 to 90:10) to obtain the title compound as a colorless oil (314 mg, 84%). MS (ISP) 392.3 (M+H)+.

Aufarbeitung

extractionthe mixture was extracted with ether
dry with materialThe combined ether layers were dried (Na2SO4)
customevaporated
customthe remaining residue was purified by chromatography (pentane/ether 100:0 to 90:10)

Quellen und Nachweise

ORD-Eintrag: ord-a17b959c3109486ba4c2f84f8763b206
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07745477B2

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