反应详情

9.21 g (35 mmol) of triphenylphosphine, 4.50 g (32 mmol) of 1,8-nonadiene-5-ol (8), and 6.03 g (41 mmol) of phthalimide were dissolved in 150 ml of tetrahydrofuran. This solution thus obtained was stirred for 30 minutes, and at room temperature, 15 ml (33 mmol) of diethyl azodicarboxylate (2.2 mol/l solution in toluene) was thereafter dropped in the solution, which was then stirred for 12 hours. Subsequently, hexane was added to the solution, and a precipitate was filtered off, and the filtrate thus obtained was dried over sodium sulfate. The solvent was distilled off, and the crude product thus obtained was purified by silica gel column chromatography (eluent: hexane:ethyl acetate of 5:1). The product thus obtained was dissolved in 50 ml of methanol, and 3 ml of hydrazine hydrate was added to the solution thus obtained, which was then refluxed for 1 hour. The reaction solution thus obtained was cooled, and a white precipitate was obtained by filtration and was washed with methanol. The filtrate thus obtained was concentrated, hexane was then added to the filtrate, and a white precipitate thus produced was obtained by re-filtration and was washed with hexane. Then, the solvent was distilled off from this filtrate. Thus, 2.58 g (18 mmol) of a slightly yellow liquid was obtained as an intended compound (9). A yield of the compound (9) was 57%. 1,8-nonadiene-5-ol (8) as a synthetic starting material can be synthesized in the same manner as in Reference Example 8 (synthesis of starting material for Example 13) described below, for example. Values obtained by instrumental analysis of the compound (9) are shown below.

1. customThis solution thus obtained
2. stirringwas then stirred for 12 hours
3. filtrationa precipitate was filtered off
4. customthe filtrate thus obtained
5. dry with materialwas dried over sodium sulfate
6. distillationThe solvent was distilled off
7. customthe crude product thus obtained
8. customwas purified by silica gel column chromatography (eluent: hexane:ethyl acetate of 5:1)
9. customThe product thus obtained
10. customthus obtained
11. temperaturewhich was then refluxed for 1 hour
12. customThe reaction solution thus obtained
13. temperaturewas cooled
14. customa white precipitate was obtained by filtration
15. washwas washed with methanol
16. customThe filtrate thus obtained
17. concentrationwas concentrated
18. additionhexane was then added to the filtrate
19. customa white precipitate thus produced
20. customwas obtained by re-filtration
21. washwas washed with hexane
22. distillationThen, the solvent was distilled off from this filtrate