Synthesis of (5Z,7E)-dodecane-5,7-diene-1-alcohol as well as acetate and propionate thereof
A technology of ethyl dienoate and dodecane, applied in the field of insect pheromone synthesis, can solve problems such as harsh reaction conditions and lengthy steps
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Embodiment 1
[0027] Synthesis of 2-heptyn-1-ol (3)
[0028] Under the protection of argon, propynyl alcohol (20mmol, 1.12g) was dissolved in dry tetrahydrofuran (20mL), and HMPA (60mmol, 10.75g) was added at room temperature, and stirred evenly. Then the temperature of the mixture was lowered to -78°C, and n-butyllithium (40mmol, 2.4M in n-hexane, 16.7mL) was slowly added dropwise. After the dropwise addition was completed, the temperature was slowly raised to -30°C, and the reaction was stirred for 1 h, then n-bromobutane (10 mmol, 1.37 g) was added, the temperature of the reaction mixture was raised to room temperature, and the reaction was stirred for 9 h. After the reaction is complete, use saturated NH 4 The reaction was quenched with aqueous Cl solution, the layers were separated, the aqueous phase was extracted with diethyl ether (3×20 mL), and the organic phases were combined. Anhydrous Na for organic phase 2 SO 4 Drying and concentration under reduced pressure gave the crude p...
Embodiment 2
[0030] Synthesis of (E)-2-hepten-1-ol (4)
[0031] Under the protection of argon, weigh lithium aluminum tetrahydrogen (2mmol, 76mg) into the Shrek bottle, lower the temperature of the system to 0°C, and slowly add (E)-2-hepten-1-ol (4) (1mmol , 114mg) in THF (4mL). The reaction was stirred at 0° C. for 1 h, then the temperature was naturally raised to room temperature, and the stirring reaction was continued for 9 h. After the reaction was completed, methanol and ammonium chloride were added to quench the reaction at 0°C. Suction filtration, the solid was washed with ether, the filtrate was extracted with ether (3×10 mL), the layers were separated, and the organic phases were combined. Anhydrous Na for organic phase 2 SO 4 Drying, concentration under reduced pressure, and finally purification by silica gel column chromatography (petroleum ether / ethyl acetate 5:1) gave (E)-2-hepten-1-ol (4) (91.8mg, yield 82%), as colorless liquid. 1 H NMR (300MHz, CDCl 3 )δ5.70-5.53(m,...
Embodiment 3
[0033] Synthesis of (5Z,7E)-dodeca-5,7-dienoic acid ethyl ester (5)
[0034] Under the protection of argon, 4A molecular sieve (0.2g) and PDC oxidant (1.3mmol, 489mg) were added into the Shrek bottle, and (E)-2-hepten-1-ol (4) (1mmol, 114mg) was added dropwise Dichloromethane (5 mL) solution was stirred at room temperature for 9 h. After the completion of the reaction, filter with suction, wash the solid with dichloromethane, wash the filtrate with saturated aqueous sodium chloride (5 mL), separate the layers, and combine the organic phases. Anhydrous Na for organic phase 2 SO 4 Dry and concentrate under reduced pressure to obtain the crude product of (E)-2-heptenal as a pale yellow liquid.
[0035] Under the protection of argon, weigh (5-ethoxy-5-oxopentyl)triphenylphosphine bromide (2 mmol, 940 mg) into a Shrek bottle, add THF (5 mL), and stir well. The temperature of the mixture was lowered to -78°C, sodium bistrimethyldisilazide (1.8mmol, 2M in THF, 0.9mL) was added sl...
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