Reaktion #73436

Reaktionsgleichung

Methyl iodide

N-butyllithium

(5-Cyclopropyl-isoxazol-3-yl)-carbamic acid phenyl ester

dry ice acetone

→

title compound

(5-Cyclopropyl-4-methyl-isoxazol-3-yl)-carbamic acid phenyl ester

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeflushed with nitrogen
2. 2
   SonstigeThe reaction is quenched (0° C.) with 20 mL of a saturated solution of ammonium chloride
3. 3
   workup.ADDITIONdiluted with ethyl acetate
4. 4
   Sonstigethe organic layer is removed
5. 5
   Trocknendried (sodium sulfate)
6. 6
   Einengenconcentrated to an oil that
7. 7
   Sonstigeis purified via FCC (0-40% ethyl acetate:heptanes)

Vorschrift

(5-Cyclopropyl-isoxazol-3-yl)-carbamic acid phenyl ester (0.368 g, 1.51 mmol) is dissolved in THF (10 mL) and cooled to −78° C. and flushed with nitrogen. N-butyllithium (2.17 mL, 3.47 mmol) is then added. The mixture is stirred in the dry ice/acetone bath for 30 minutes. Methyl iodide (0.10 mL, 1.66 mmol) is added neat and the reaction is stirred for 2 hours at −78° C. The reaction is quenched (0° C.) with 20 mL of a saturated solution of ammonium chloride, diluted with ethyl acetate and the organic layer is removed, dried (sodium sulfate) and concentrated to an oil that is purified via FCC (0-40% ethyl acetate:heptanes) to give the title compound as an oil. MS (ESI) m/z 259.20 (M+1).

Quelle