Reaktion #2303473

Reaktionsgleichung

tetrabutylammonium fluoride

trifluoromethyl-trimethylsilane

cesium carbonate

6-[4-(benzo[1,3]dioxol-4-yl)-4-methyl-2-oxo-valeroyl-amino]-4-methyl-2,3-benzoxazin-1-one

→

title compound

(±)-6-[4-(Benzo[1,3]dioxol-4-yl)-2-hydroxy-4-methyl-2-trifluoromethyl-valeroyl-amino]-4-methyl-2,3-benzoxazin-1-one

Lösungsmittel

water

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwhile being cooled with ice
2. 2
   workup.STIRRINGit is stirred for one hour at room temperature
3. 3
   Extraktionit is extracted with ethyl acetate
4. 4
   Trocknenthe organic phase is dried (Na2SO4)
5. 5
   Einengenconcentrated by evaporation
6. 6
   SonstigeThe crude product is chromatographed on silica gel

Vorschrift

2.67 g of 6-[4-(benzo[1,3]dioxol-4-yl)-4-methyl-2-oxo-valeroyl-amino]-4-methyl-2,3-benzoxazin-1-one is dissolved under argon in 35 ml of dimethylformamide and mixed with 4.66 ml of trifluoromethyl-trimethylsilane and 2.6 g of cesium carbonate while being cooled with ice. After 18 hours of stirring at room temperature, a spatula tip full of tetrabutylammonium fluoride is added, and it is stirred for one hour at room temperature. After 300 ml of water is added, it is extracted with ethyl acetate, the organic phase is dried (Na2SO4) and concentrated by evaporation. The crude product is chromatographed on silica gel. With hexane/ethyl acetate (80:20), 1.33 g of the title compound is obtained in a pure state.

Quelle