Реакция #69435

Уравнение реакции

water

Tetrafluoroboric acid

iodobenzene diacetate

2-Cyclopentene-1-acetic acid

→

title compound

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

Растворители

acetic acid

Условия реакции

Обработка

1. 1
   Экстракцияextracted with chloroform
2. 2
   ЭкстракцияThe chloroform layer was extracted with water
3. 3
   СушкаThe combined organic layers were dried (magnesium sulfate)
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   ДругоеThe residue was purified by silica gel chromatography (Biotage 40M)
7. 7
   Промывкаeluting with 0-100% ethyl acetate/hexanes

Методика

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).

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