반응 #69435

반응 방정식

water

Tetrafluoroboric acid

iodobenzene diacetate

2-Cyclopentene-1-acetic acid

→

title compound

cis-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one

용매

acetic acid

반응 조건

후처리

1. 1
   추출extracted with chloroform
2. 2
   추출The chloroform layer was extracted with water
3. 3
   건조The combined organic layers were dried (magnesium sulfate)
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   기타The residue was purified by silica gel chromatography (Biotage 40M)
7. 7
   세척eluting with 0-100% ethyl acetate/hexanes

실험 절차

Tetrafluoroboric acid (2.50 mL, 15.9 mmol) was added to a solution of iodobenzene diacetate (5.10 g, 15.9 mmol) in acetic acid (13.2 mL). 2-Cyclopentene-1-acetic acid (955 μL, 7.93 mmol) was added and the solution was stirred at room temperature for 1 hour. The solution was then added to water and extracted with chloroform. The chloroform layer was extracted with water. The combined organic layers were dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (Biotage 40M), eluting with 0-100% ethyl acetate/hexanes to give the title compound as a colorless oil. 1H NMR (500 MHz, CHCl3) δ 2.22-2.31 (m, 2H), 2.67-2.84 (m, 2H), 3.05-3.15 (m, 1H), 5.44-5.51 (m, 1H), 5.79-5.86 (m, 1H), 6.01-6.07 (m, 1H).

출처