반응 #359515

반응 방정식

3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine

sodium carbonate

→

title compound

수율 65.2%

6-[3-(4-Isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl]-6,7-dihydro-5H-[1,3]dioxolo[4,5-f]isoindole

수율 65.2%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도the mixture was refluxed
2. 2
   온도with heating for 23 hours
3. 3
   추출The product was extracted twice with ethyl acetate
4. 4
   세척The combined extracts were washed with an aqueous saturated solution of sodium hydrogen carbonate
5. 5
   기타dried on magnesium sulfate
6. 6
   여과filtered
7. 7
   농축concentrated under reduced pressure
8. 8
   기타The residue was crystallized from isopropyl ether

실험 절차

To a solution of 3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine (835.5 mg, 2.58 mmol) in tetrahydrofuran (20 ml) were added 5,6-bis(chloromethyl)-1,3-benzodioxazole (574.5 mg, 2.62 mmol), sodium carbonate (832.8 mg, 7.88 mmol), and tetrabutylammonium iodide (481.6 mg, 1.30 mmol) and the mixture was refluxed with heating for 23 hours. The reaction mixture was cooled down to room temperature and then poured into ice water. The product was extracted twice with ethyl acetate. The combined extracts were washed with an aqueous saturated solution of sodium hydrogen carbonate, dried on magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was crystallized from isopropyl ether to obtain 395.0 mg (33% yield) of the title compound. Melting point: 175-177° C.

출처