反应详情

温度

0 °C

10 g 1,9-cyclohexadecadiene of the following composition are added to a solution of 14.1 g sodium acetate in 75 ml methylene chloride and the mixture is cooled to 0° C.: (Z,Z)-1,9-cyclohexadecadiene 18%, (E,Z)-1,9-cyclohexadecadiene 54%, (E,E)-1,9-cyclohexadecadiene 28%. 8.6 g peracetic acid (40% strength) in 15 ml methylene chloride are slowly added dropwise at this temperature and the mixture is subsequently stirred for three hours at 0° C. The reaction solution is poured on to ice-water and extracted once with methylene chloride. The combined organic phases are washed with saturated NaCl solution and subsequently dried with magnesium sulfate, and after removal of the solvent 9.0 g of crude product are obtained. After purification by chromatography with ethyl acetate/cyclohexane, a product having the following composition is obtained: (E)-17-oxabicyclo[14.1.0]heptadec-8-ene (1) 33%, (E)-17-oxabicyclo[14.1.0]heptadec-8-ene (2) 28%, (Z)-17-oxabicyclo[14.1.0]heptadec-8-ene (3) 21%, (Z)-17-oxabicyclo[14.1.0]heptadec-8-ene (4) 18%.

1. extractionextracted once with methylene chloride
2. washThe combined organic phases are washed with saturated NaCl solution
3. dry with materialsubsequently dried with magnesium sulfate
4. customafter removal of the solvent 9.0 g of crude product
5. customare obtained
6. customAfter purification by chromatography with ethyl acetate/cyclohexane
7. customis obtained