non-2-ene

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dissolve 33.1 g (0.2 mol) of N-[(E)-2,4-pentadienyl]-N-(2-propenyl)-acetamide (title compound from Example A.3.) in 200 ml of xylene, pass a powerful stream of nitrogen through for 15 min, add 0.1 g of 4-hydroxyanisole, and then heat to reflux overnight. Concentrate, distil under high vacuum.

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To obtain an olefin further enriched in trans-2-nonene, 8.9 g (91 mmoles) of Olefin Product 1 treated with 12.6 g (70 mmoles) of the anthracene, as described above, to form a Diels-Alder adduct with the 2-nonene. By distillation, as above, 3.3 g (33 mmoles) of Unreacted Olefins 3 was separated from the crude nonene-anthracene mixture. The remaining nonene-anthracene adduct was thermally dissociated, as described above, and 3.7 g (37 mmoles) of Olefin Product 3 recovered. Olefin Product 3 was further enriched in trans-2-nonene. Olefin Product 3 contained 97.2% trans-2-nonene compared with 75.6% in the original feedstock and 91.9% in Olefin Product 1.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a toluene solution (84.0 ml) of 2,6-di-tert-butyl-4-methylphenol (9.78 g, 44.5 mmol), diisobutylaluminum hydride (1.5M toluene solution, 18.5 ml, 27.8 mmol) was dropwise added over a period of 30 minutes under an argon atmosphere at 0° C. Then, the mixture was stirred at the same temperature for 90 minutes. Then, at -78° C., a toluene solution (30.0 ml) of 3-(3-oxa-4-tert-butoxycarbonylbutyl)-7-exo-(2-chloro-4,4-dimethyl-3-oxo-1-nonen-6-ynyl)-8-endo-hydroxy-cis-bicyclo[4.3.0]non-2-ene (1.37 g, 2.78 mmol) was dropwise added to the reaction solution over a period of 10 minutes. Then the temperature was raised from -78° C. to -60° C. over a period of two hours. To the reaction solution, a saturated sodium chloride aqueous solution was added, and the mixture was stirred for a while. Then, the mixture was extracted with ethyl acetate, and the organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue thereby obtained was purified by silica gel column chromatography (ethyl ether : n-hexane =1 : 1-2) to obtain 3-(3-oxa-4-tert-butoxycarbonylbutyl)-7-exo-(2-chloro-4,4-dimethyl-3α-hydroxy-1-nonen-6-ynyl)-8-endo-hydroxy-cis-bicyco[4.3.0]non-2-ene (1.18 g, 86.0%) as a highly porous component and 3-(3-oxa-4-tert-butoxycarbonylbutyl)-7-exo-(2-chloro-4,4-dimethyl-3β-hydroxy-1-nonen-6-ynyl)-8-endo-hydroxy-cis-bicyclo[4.3.0]non-2-ene (0.16 g, 11.6%) as a low polar component, each as a slightly yellow oily substance. The spectrum data of the α-epimer are shown below. The spectrum data of the β-epimer were substantially the same as α-epimer. Then the temperature was raised from -78° C. to -60° C. over a period of two hours the mixture was stirred for a while Then, the mixture was extracted with ethyl acetate the organic layer was washed with water a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate Then, the solvent was distilled off under reduced pressure the residue thereby obtained was purified by silica gel column chromatography (ethyl ether : n-hexane =1 : 1-2)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dissolve 33.1 g (0.2 mol) of N-[(E)-2,4-pentadienyl]-N-(2-propenyl)-acetamide (title compound from Example A.3.) in 200 ml of xylene, pass a powerful stream of nitrogen through for 15 min, add 0.1 g of 4-hydroxyanisole, and then heat to reflux overnight. Concentrate, distil under high vacuum.