Réaction #2161613

Équation de réaction

2-propylbenzene-1,3-diol

ethyl 4,4,4-trifluoroacetoacetate

→

title compound

Rendement 77.0%

7-hydroxy-8-propyl-4-(trifluoromethyl)-2H-chromen-2-one

Rendement 77.0%

Solvants

water

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate
2. 2
   LavageSubsequently, the organic layer was washed with saturated saline
3. 3
   Autredried
4. 4
   Concentrationconcentrated under vacuum
5. 5
   AutreThe obtained residue was purified
6. 6
   Autrerecrystallized with chloroform

Mode opératoire

2-propylbenzene-1,3-diol (J. Med. Chem., 38, pp 4411-4432, 1995) (3.65 g, 24.0 mmol), zinc chloride (3.60 g, 26.4 mmol), and ethyl 4,4,4-trifluoroacetoacetate (4.86 g, 26.4 mmol) were stirred overnight at 110° C. The reaction solution was added with water and extracted with ethyl acetate. Subsequently, the organic layer was washed with saturated saline, dried using anhydrous sodium sulfate, and concentrated under vacuum. The obtained residue was purified using silica-gel chromatography (chloroform) and then recrystallized with chloroform, and 5.01 g of the title compound (yield 77%) was obtained as pale-brown crystalline powder.

Source