Reaktion #828877

Reaktionsgleichung

product

(Z)-N,O-di-tert-butoxycarbonyl-N-[3-(3-[4,5-dihydro-5-(4-fluorophenyl)isoxazol-3-yl]phenyl)-2-propen-1-yl]-N-hydroxylamine

trimethylsilyl trifluoromethanesulfonate

→

title compound

Ausbeute 93.0%

(Z)-N-[3-(3-[4,5-dihydro-5-(4-fluorophenyl)isoxazol-3-yl]phenyl)-2-propen-1-yl]-N-hydroxylamine

Ausbeute 93.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe organic layer was separated
2. 2
   Extraktionthe aqueous layer was extracted with CH2Cl2 (30 ml×3)
3. 3
   WaschenThe combined extracts were washed with aqueous NaHCO3 (50 ml) and brine (50 ml)
4. 4
   Trocknenwas dried (MgSO4) and solvent
5. 5
   Sonstigewas removed under reduced pressure

Vorschrift

To a solution of the product of Step 4, above (16, 3.2 g, 6.2 mmol) in CH2Cl2 (30 ml) cooled to 0° C., was slowly added trimethylsilyl trifluoromethanesulfonate (2.5 ml, 13.4 mmol) under a nitrogen atmosphere. The reaction mixture was allowed to warm to room temperature and was stirred for 1.5 hours. The reaction mixture was poured carefully into ice cold water (30 ml), the organic layer was separated and the aqueous layer was extracted with CH2Cl2 (30 ml×3). The combined extracts were washed with aqueous NaHCO3 (50 ml) and brine (50 ml), then was dried (MgSO4) and solvent was removed under reduced pressure to afford the title compound (17, (1.8 g, 93% yield) as pale yellow solids.

Quelle