2-Cyclopentene-1-ol → 3-(3-(5-Phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)cyclopentanone

Participants

Reaction Conditions

Reaction Steps

To a mixture of 7-iodo-3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazole (Preparation 121B, 370 mg, 0.728 mmol), tetrabutylammonium chloride (202 mg, 0.728 mmol), potassium acetate (214 mg, 2.184 mmol), and anhydrous DMF (2 mL) was bubbled with nitrogen for 3 min. before palladium (II) acetate (16.34 mg, 0.073 mmol) and cyclopent-2-enol (122 mg, 1.456 mmol) were added. The mixture was bubbled for 2 min. and sealed in a 2-dram vial. The mixture was stirred at 75° C. for 3 h. The mixture was cooled, diluted with water (30 ml) and extracted with ethyl acetate (3×10 mL). The combined ethyl acetate extracts were dried (sodium sulfate) and concentrated under reduced pressure. Flash chromatography purification (silica gel column, 5→50% ethyl acetate in n-heptane) afforded 3-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-4,5-dihydronaphtho[1,2-c]isoxazol-7-yl)cyclopentanone (230 mg, 0.495 mmol, 68.0% yield). The compound had an HPLC retention time=4.04 min. (condition C); LC/MS M+1=465.2.

Provenance & Evidence