反应 #553820

反应方程式

farnesol

triethylamine

→

clear oil

收率 100.0%

(E,E)-3,7,11-Trimethyl-2,6,10-dodecatrienaldehyde

收率 100.0%

溶剂

water

反应条件

后处理

1. 1
   workup.STIRRINGAfter stirring for an additional 15 minutes at -65° C.
2. 2
   温度the reaction was warmed to room temperature
3. 3
   萃取The resulting aqueous layer was extracted several times with CH2Cl2
4. 4
   洗涤The combined organic layers were washed once with saturated aqueous NaCl solution, once with 1% HCl, once with 5% Na2CO3 solution and once with saturated aqueous NaCl solution
5. 5
   干燥The resulting organic layer was dried over MgSO4

实验过程

A solution of oxalyl chloride (4.68 g, 0.037 mol) in dry CH2Cl2 under argon atmosphere was cooled to -65° C. A solution of 5.33 mL of dimethyl sulfoxide (DMSO) (0.68 mol) in CH2Cl2 (17 mL) was added rapidly, dropwise, to the cooled oxalyl chloride solution. After stirring for 7 minutes at -65° C., a 10 mL CH2Cl2 solution of (E,E)-farnesol (7.0 g, 0.032 mol) was added over 10 minutes to the reaction solution at -65° C.: a precipitate formed upon the addition of approximately half of the farnesol solution. After the addition of the farnesol solution was completed, the reaction was stirred at -65° C. for 25 minutes, and then 22.4 mL (0.16 mol) of triethylamine was added over 10 minutes. After stirring for an additional 15 minutes at -65° C., the reaction was warmed to room temperature, and then diluted with water (~200 mL). The resulting aqueous layer was extracted several times with CH2Cl2. The combined organic layers were washed once with saturated aqueous NaCl solution, once with 1% HCl, once with 5% Na2CO3 solution and once with saturated aqueous NaCl solution. The resulting organic layer was dried over MgSO4 to give 7.05 g (100%) of a clear oil after filtration and solvent removal.

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