3,5-Dimethylisoxazole → 2-(3-Methyl-isoxazol-5-yl)-1-(2-tert.butyldimethylsiloxy-phenyl)-ethanone

HRID 54421

Reaktionsgleichung

C([Li])CCC.[CH3:6][C:7]1[CH:11]=[C:10]([CH3:12])[O:9][N:8]=1.[C:13]([C:17]1[C:26]([O:27][SiH:28]([CH3:30])[CH3:29])=[CH:25][CH:24]=[CH:23][C:18]=1[C:19](OC)=[O:20])([CH3:16])([CH3:15])[CH3:14].[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH3:6][C:7]1[CH:11]=[C:10]([CH2:12][C:19]([C:18]2[CH:23]=[CH:24][CH:25]=[C:26]([O:27][SiH:28]([CH3:30])[CH3:29])[C:17]=2[C:13]([CH3:16])([CH3:15])[CH3:14])=[O:20])[O:9][N:8]=1

Komponenten

Reaktionsbedingungen

Temperatur: -20 °C

Versuchsvorschrift

52 ml of 1N solution of n-butyllithium in hexane were added to a solution of 6 g of 3,5-dimethylisoxazol in 200 ml of tetrahydrofuran at -78° C. After stirring for 1 h 15 g of methyl 2-tert.butyldimethylsiloxybenzoate in 50 ml of tetrahydrofuran were added at the same temperature. The reaction mixture was slowly warmed up to -20° C. A saturated aqueous solution of ammonium chloride was added, the mixture was extracted several times with ethylacetate. The organic phase was separated, washed with water and dried over magnesium sulfate. Chromatography on silica gel with heptane/ethylacetate gave 9.4 g of the product.

Aufarbeitung

additionwere added at the same temperature
extractionthe mixture was extracted several times with ethylacetate
customThe organic phase was separated
washwashed with water
dry with materialdried over magnesium sulfate

Quellen und Nachweise

ORD-Eintrag: ord-a7602e0c89e6449eacff8936f61394cd
Quelldatensatz: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05622953

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