Реакция #631989

Уравнение реакции

α-damascone

N,N-dimethylaminoethanol

tetramethylguanidine

→

product

Выход 32.0%

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

Выход 32.0%

Условия реакции

Обработка

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
   Экстракцияthis mixture was extracted with 5% aqueous HCl
4. 4
   Промывкаwashed with water and saturated aqueous NaCl
5. 5
   Экстракцияextracted twice with ether
6. 6
   Другоеto recover the crude product in the organic phases
7. 7
   ПромывкаThe organic phases were still washed with water and brine
8. 8
   Сушкаdried over Na2SO4
9. 9
   Концентрированиеconcentrated
10. 10
    workup.DISTILLATIONBulb-to-bulb distillation of the crude product (100-125° C./0.05 mbar)

Методика

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%).

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