Reaktion #163218

Reaktionsgleichung

Water

Methanol

(4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-acetic acid ethyl ester

DIBAL-H

→

title compound

Ausbeute 56.2%

(4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-acetaldehyde

Ausbeute 56.2%

Lösungsmittel

Rochelle's salt

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto quench
2. 2
   Sonstigethe reaction
3. 3
   workup.ADDITIONThe reaction mixture is then poured in ice
4. 4
   Extraktionthe mixture is extracted with EtOAc (3×30 mL)
5. 5
   WaschenThe organic phase is washed with brine (3×30 mL)
6. 6
   Trocknendried with Na2SO4
7. 7
   Einengenconcentrated

Vorschrift

To a solution of (4-{4-[2-(3-Chlorophenylamino)-oxazol-5-yl]-phenyl}-cyclohexyl)-acetic acid ethyl ester (500 mg, 1.14 mmol) in DCM (20 mL) at −78° C. is added DIBAL-H (1 M in toluene, 2.14 mL, 2.14 mmol) and the mixture is allowed to stir at −78° C. for 2 h. Methanol (3 mL) is added to quench the reaction. The reaction mixture is then poured in ice and Rochelle's salt (4 g). Water (20 mL) is added and the mixture is extracted with EtOAc (3×30 mL). The organic phase is washed with brine (3×30 mL), dried with Na2SO4 and concentrated to give the title compound (253 mg) as a white solid: (M+H)+395.2.

Quelle