Réaction #69435

Équation de réaction

water

Tetrafluoroboric acid

iodobenzene diacetate

2-Cyclopentene-1-acetic acid

→

title compound

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

Solvants

acetic acid

Conditions de réaction

Traitement

1. 1
   Extractionextracted with chloroform
2. 2
   ExtractionThe chloroform layer was extracted with water
3. 3
   SéchageThe combined organic layers were dried (magnesium sulfate)
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutreThe residue was purified by silica gel chromatography (Biotage 40M)
7. 7
   Lavageeluting with 0-100% ethyl acetate/hexanes

Mode opératoire

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).

Source