Reaktion #430728

Reaktionsgleichung

4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-(2-pyridylethynyl)cyclohexane

pyridinium p-toluenesulfonate

→

4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(2-pyridylethynyl)cyclohexan-1-one

Lösungsmittel

acetone

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas refluxed for three days
2. 2
   Sonstigewas evaporated
3. 3
   workup.ADDITIONWater was added
4. 4
   Extraktionthe mixture was extracted three times with dichloromethane
5. 5
   Trocknenthe extract was dried (magnesium sulfate)
6. 6
   Sonstigewas evaporated
7. 7
   SonstigePurification by flash chromatography
8. 8
   Wascheneluting with 25:75 ethyl acetate

Vorschrift

A mixture of 4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-(2-pyridylethynyl)cyclohexane (0.17 g, 0.39 mmol) and pyridinium p-toluenesulfonate (0.10 g, 0.39 mmol) in acetone (4 mL) and water (1 mL) was refluxed for three days, then was evaporated. Water was added, the mixture was extracted three times with dichloromethane, the extract was dried (magnesium sulfate) and was evaporated. Purification by flash chromatography, eluting with 25:75 ethyl acetate:hexanes, provided 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(2-pyridylethynyl)cyclohexan-1-one as a wax. 1H-NMR (400 MHz, CDCl3) δ 8.61 (d, J=4.8 Hz, 1H), 7.68 (dt, J=7.8, 1.8 Hz, 1H), 7.47 (d, J=7.8 Hz, 1H), 7.27 (m, 1H), 7.20 (d, J=2.3 Hz, 1H), 7.15 (dd, J=8.5, 2.4 Hz, 1H), 6.87 (d, J=8.5 Hz, 1H), 4.81 (m, 1H), 3.85 (s, 3H), 3.07 (dt, J=14.4, 5.8 Hz, 2H), 2.49 (d, J=14.8 Hz, 2H), 2.41 (m, 2H), 2.27 (dt, J=13.4, 3.9 Hz, 2H), 1.8-2.0 (m, 6H), 1.61 (m, 2H). Anal. (C25H27NO3.0.65 H2O) calcd: C, 74.84; H, 7.11; N, 3.49; found: C, 75.00; H, 6.83; N, 3.52.

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