反应 #631989

反应方程式

α-damascone

N,N-dimethylaminoethanol

tetramethylguanidine

→

product

收率 32.0%

3-[2-(dimethylamino)ethoxy]-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone

收率 32.0%

反应条件

后处理

1. 1
   workup.DISTILLATIONAfterward, the excess of N,N-dimethylaminoethanol was distilled at ca. 60° C./10 to 2 mbar
2. 2
   workup.ADDITIONThe crude product was diluted in diethyl ether (Et2O)
3. 3
   萃取this mixture was extracted with 5% aqueous HCl
4. 4
   洗涤washed with water and saturated aqueous NaCl
5. 5
   萃取extracted twice with ether
6. 6
   其他to recover the crude product in the organic phases
7. 7
   洗涤The organic phases were still washed with water and brine
8. 8
   干燥dried over Na2SO4
9. 9
   浓缩concentrated
10. 10
    workup.DISTILLATIONBulb-to-bulb distillation of the crude product (100-125° C./0.05 mbar)

实验过程

A solution of α-damascone (6.44 g; 33.5 mmol), N,N-dimethylaminoethanol (30.25 ml; 301 mmol) and tetramethylguanidine (TMG) (0.77 g; 6.70 mmol) was heated at 70° C. for 15 h. Afterward, the excess of N,N-dimethylaminoethanol was distilled at ca. 60° C./10 to 2 mbar. The crude product was diluted in diethyl ether (Et2O) and this mixture was extracted with 5% aqueous HCl and washed with water and saturated aqueous NaCl. The combined aqueous phases were basified using aqueous NaOH and extracted twice with ether to recover the crude product in the organic phases. The organic phases were still washed with water and brine, then dried over Na2SO4 and concentrated. Bulb-to-bulb distillation of the crude product (100-125° C./0.05 mbar) afforded 2.94 g of the desired pure product (yield: 32%).

来源