Synthetic method of sex pheromone intermediates of American white moth
A technology of American white moth and synthetic method, which is applied in the direction of organic chemistry, organic chemistry, etc., can solve the problems of difficult control of the reaction process, difficult operation, high reactivity, etc., and achieve strong reaction operability, lower production costs, and better reaction conditions mild effect
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Embodiment 1
[0036] Embodiment 1, a kind of preparation method of white moth sex pheromone intermediate (2S, 3R)-2,3-epoxy-1-tetradecyl alcohol, carries out the following steps successively:
[0037] Step 1, Synthesis of (Z)-2-enetetradec-1-alcohol (3)
[0038]
[0039] At 20°C, add nickel acetate tetrahydrate (2.5mmol, 623mg), sodium borohydride (11mmol, 418mg), ethylenediamine (13.5mmol, 0.9mL) and 150mL 95% ethanol to a 500mL hydrogenation reaction kettle in sequence, mix and stir 20 minutes. Then add 100 mL of 95% ethanol solution dissolved in 2-alkynetetradec-1-ol (2) (25 mmol, 5.25 g) to replace the hydrogen, and the reaction pressure is 0.2 MPa, and the reaction is continued for 20 hours.
[0040] After the reaction is complete, the reaction solution is filtered to remove the catalyst (nickel boride), the filter cake is washed with ethyl acetate (10ml), and the filtrate is concentrated and dried under reduced pressure (at a pressure of 0.1Mpa and at a temperature of 40°C for 120...
Embodiment 2
[0050] Embodiment 2, a kind of preparation method of white moth sex pheromone intermediate (2S, 3R)-2,3-epoxy-1-tetradecyl alcohol, the following steps are carried out in sequence:
[0051] Step 1, Synthesis of (Z)-2-enetetradec-1-alcohol (3)
[0052]
[0053] 95% ethanol in step 1) of embodiment 1 is changed into methanol (volume constant), reaction temperature is changed into 25 ℃, reaction pressure is changed into 0.5MPa, all the other are equal to embodiment 1.
[0054] The purity of compound 3 is 82%, Z / E>85.
[0055] Step 2. Synthesis of (2S,3R)-2,3-epoxy-1-14 carbon alcohol (4)
[0056]
[0057] The dichloromethane in step 2) of Example 1 was changed to chloroform (volume constant), the reaction temperature was changed to 25° C., and the rest were the same as in Example 1.
[0058] Compound 4 has dr>10, ee=80%.
Embodiment 3
[0059] Embodiment 3, " sodium bicarbonate " solution in embodiment 1 step 2) is correspondingly changed into " potassium bicarbonate, sodium carbonate, potassium carbonate or cesium carbonate " solution, concentration is constant, and volume is also constant; Identical to step 2) of Example 1; The results obtained are shown in Table 1 below.
[0060] Table 1
[0061] carbonate Compound 4dr ee sodium bicarbonate >13 85% potassium bicarbonate >13 85% Sodium carbonate >12 82% potassium carbonate >12 82% cesium carbonate >12 80%
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