반응 #8296

반응 방정식

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

용매

ether

dichloromethane

dichloromethane

반응 조건

후처리

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

실험 절차

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.

출처