Ethyl Acetate → [4-(4-Dimethylsulfamoyl-benzoyl)-naphthalen-2-yl]-acetic acid ethyl ester

HRID 1644716

Reaktionsgleichung

C(O[C:4](=O)[CH2:5][CH2:6]C=O)C.C([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]#[C:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]([CH3:31])[CH3:30])(=[O:28])=[O:27])=[CH:22][CH:21]=1)=O.[C:32]([O:35][CH2:36][CH3:37])(=[O:34])[CH3:33].[O:38]1CCOCC1>[Au](Br)(Br)Br>[CH2:36]([O:35][C:32](=[O:34])[CH2:33][C:5]1[CH:6]=[C:18]([C:19](=[O:38])[C:20]2[CH:25]=[CH:24][C:23]([S:26](=[O:27])(=[O:28])[N:29]([CH3:30])[CH3:31])=[CH:22][CH:21]=2)[C:13]2[C:12](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:4]=1)[CH3:37]

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A suspension of gold(III) bromide (38 mg, 0.087 mmol), 4-oxo-butyric acid ethyl ester (377 mg, 2.9 mmol) and 4-(2-formyl-phenylethynyl)-N,N-dimethyl-benzenesulfonamide (454 mg, 1.45 mmol) in anhydrous dioxane (10 mL) was heated at 100° C. for 4 hours. After being cooled to room temperature, the mixture was treated with ethyl acetate, and then washed with water. The collected organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (RediSep® Flash column, 230-400 mesh, 25-60% ethyl acetate in hexane) gave [4-(4-dimethylsulfamoyl-benzoyl)-naphthalen-2-yl]-acetic acid ethyl ester (180 mg, 29%). MS (ESI+) cald. for C23H23NO5S [(M+H)+] 425, obsd. 426.

Aufarbeitung

temperatureAfter being cooled to room temperature
washwashed with water
dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag: ord-5b350a69c57e4ada870ac98732ece1a2
Quelldatensatz: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08124629B2

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