Reaktion #79353

Reaktionsgleichung

ethyl 7-(3-bromopropoxy)-2-ethylchromane-2-carboxylate

3-trifluoromethyl-7-propyl-6-hydroxybenzisoxazole

cesium carbonate

→

title compound

Ausbeute 85.0%

Ethyl 7-(3-(3-trifluoromethyl-7-propyl-6-benz-[4,5]-isoxazoloxy)propoxy)-2-ethylchromane-2-carboxylate

Ausbeute 85.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed under reduced pressure
2. 2
   workup.ADDITIONThe residue was diluted with AcOEt and water
3. 3
   SonstigeThe organic layer was separated
4. 4
   Extraktionthe aqueous layer was extracted twice with AcOEt
5. 5
   TrocknenThe combined organic layers were dried over anhydrous Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   Sonstigechromatographed on silica gel
9. 9
   WaschenElution with 20% AcOEt/hexanes

Vorschrift

To a 2 ml DMF solution of ethyl 7-(3-bromopropoxy)-2-ethylchromane-2-carboxylate (40 mg, 0.108 mmol) and 3-trifluoromethyl-7-propyl-6-hydroxybenzisoxazole (U.S. Pat. No. 6,090,836) (29 mg, 0.118 mmol) was added cesium carbonate (39 mg, 0.12 mmol). The resulting suspension was heated to 70° C. for 5 hr. The solvent was removed under reduced pressure. The residue was diluted with AcOEt and water. The organic layer was separated, and the aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on silica gel. Elution with 20% AcOEt/hexanes gave the title compound as a pale yellow oil 49 mg (85%).

Quelle