Method for synthesizing sex pheromone of carposina niponensis
A technology of peach borer and synthetic method, which is applied in the direction of organic chemical methods, chemical instruments and methods, and the preparation of organic compounds, and can solve problems such as expensive reagents, lengthy reaction routes, and harsh reaction conditions
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Embodiment 1
[0029] Synthesis of 1-tetrahydropyranyloxy-3-bromopropane 2
[0030] At room temperature, add dichloromethane (200 mL) and p-toluenesulfonic acid (1.72 g, 10 mmol) into a 500 mL round bottom flask, stir to dissolve. Then 3-bromo-1-propanol (13.90g, 100mmol) and 2,3-dihydropyran (12.60g, 150mmol) were added successively, and the reaction was stirred for 12h. After the reaction was completed, water was added to quench, and the organic phase was separated. The aqueous phase was extracted with dichloromethane (3 x 100 mL), and the organic phases were combined. The organic phase was washed with saturated NaCl aqueous solution, washed with anhydrous NaCl 2 SO 4 Dry and concentrate under reduced pressure to obtain crude product. Finally, it was purified by silica gel column chromatography (petroleum ether / ethyl acetate 30:1) to obtain yellow-green oily liquid 1-tetrahydropyranyloxy-3-bromopropane 2 (19.68 g, yield 88%). 1 H NMR (300MHz, CDCl 3)δ4.67(dd,J=12.5,3.5Hz,1H),3.84–3.7...
Embodiment 2
[0032] Synthesis of 1-tetrahydropyranyloxy-4-undecyne 3
[0033] Under argon protection, add anhydrous tetrahydrofuran (100 mL) and 1-octyne (8.82 g, 80 mmol) into a 200 mL Schlenk reaction flask, and stir to dissolve. The temperature of the mixture was cooled to -40°C, and n-butyllithium (39.0 mL, 2.4M n-hexane solution, 88 mmol) was slowly added dropwise, and stirred for 4 h after the drop was completed. Then HMPA (6.83 mL, 80 mmol) was slowly added dropwise, and the reaction was stirred for 0.5 h. 1-Tetrahydropyranyloxy-3-bromopropane 2 (8.92 g, 40 mmol) was added dropwise, and after the addition was completed, the temperature was slowly raised to room temperature to continue the reaction for 24 h. After the reaction was completed, the reaction was quenched with saturated aqueous ammonium chloride solution, and the organic phase was separated. The aqueous phase was extracted with ether (3 x 80 mL), and the organic phases were combined. The organic phase was washed with s...
Embodiment 3
[0035] Synthesis of (Z)-1-tetrahydropyranyloxy-4-undecene 4
[0036] At room temperature, nickel acetate tetrahydrate (4.69 g, 26.5 mmol) was added into a 250 mL reaction flask. Vacuumize the reaction flask and fill it with hydrogen gas, slowly drop into ethanol solution of sodium borohydride (1.00 g, 26.5 mmol), and stir for 1 h. Then ethylenediamine (6.38g, 106mmol) was added dropwise, and after stirring for 10min, 1-tetrahydropyranyloxy-4-undecyne 3 (6.71g, 26.5mmol) was added dropwise, and the stirring reaction was continued for 8h. After the reaction was completed, it was concentrated under reduced pressure, the mixture was extracted with ether, and washed with anhydrous Na 2 SO 4 Dry and concentrate under reduced pressure to obtain crude product. Finally, it was purified by silica gel column chromatography (petroleum ether / ethyl acetate 50:1) to obtain light yellow oily liquid (Z)-1-tetrahydropyranyloxy-4-undecene 4 (6.62g, yield 98 %). 1 H NMR (300MHz, CDCl 3 )δ5....
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