反応 #631989

反応方程式

α-damascone

N,N-dimethylaminoethanol

tetramethylguanidine

→

product

収率 32.0%

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

収率 32.0%

反応条件

後処理

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
   抽出this mixture was extracted with 5% aqueous HCl
4. 4
   洗浄washed with water and saturated aqueous NaCl
5. 5
   抽出extracted twice with ether
6. 6
   その他to recover the crude product in the organic phases
7. 7
   洗浄The organic phases were still washed with water and brine
8. 8
   乾燥dried over Na2SO4
9. 9
   濃縮concentrated
10. 10
    workup.DISTILLATIONBulb-to-bulb distillation of the crude product (100-125° C./0.05 mbar)

実験手順

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%).

出典