Реакция #8296

Уравнение реакции

borontrifluoride etherate

4-(5-methoxy-tetrahydro-furan-3-yl)-benzoic acid ethyl ester

3-chloroperbenzoic acid

magnesium sulfate

→

title compound

4-(5-Oxo-tetrahydro-furan-3-yl)-benzoic acid ethyl ester

Растворители

ether

dichloromethane

dichloromethane

Условия реакции

Обработка

1. 1
   ДругоеSolids are removed by filtration
2. 2
   workup.STIRRINGThe mixture is stirred at room temperature 18 h
3. 3
   Промывкаwashed with a 10% solution of sodium thiosulfite (150 mL)
4. 4
   СушкаThe mixture is dried over magnesium sulfate
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated in vacuo
7. 7
   ДругоеThe residue is chromatographed on SiO2 (elute with 20% ethyl acetate/hexanes)

Методика

To a solution of 75% 3-chloroperbenzoic acid (2.7 g, 11.76 mmol) in dichloromethane (35 mL) is added magnesium sulfate (2.0 g, 16.6 mmol) and the mixture stirred for 30 min. Solids are removed by filtration and the filtrate treated with borontrifluoride etherate (0.5 mL, 3.92 mmol) and 4-(5-methoxy-tetrahydro-furan-3-yl)-benzoic acid ethyl ester (2.45 g, 9.8 mmol) in dichloromethane (5 mL). The mixture is stirred at room temperature 18 h, diluted with ether (200 mL) and washed with a 10% solution of sodium thiosulfite (150 mL), a saturated solution of sodium bicarbonate (150 mL) and brine. The mixture is dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is chromatographed on SiO2 (elute with 20% ethyl acetate/hexanes) to yield the title compound, 2.2 g (96%), as an off-white solid.

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