Реакция #341717

Уравнение реакции

butyl-[1-(2,6-difluoro-phenyl)-meth-(E)-ylidene]-amine

ether

cyclopropylmagnesium bromide

diethyl ether

cyclopropylmagnesium bromide

cyclopropyl bromide

magnesium

diethyl ether

→

title compound

Выход 64.0%

2,6-Dicyclopropyl-benzaldehyde

Выход 64.0%

Условия реакции

Обработка

1. 1
   ДругоеThis compound was prepared
2. 2
   Другоеdescribed in Synthesis 1999, 2138-2144
3. 3
   Температураby heating
4. 4
   Температураat reflux for 5 min
5. 5
   workup.ADDITIONAfter the addition
6. 6
   Температураfor 90 minutes at reflux
7. 7
   ТемператураThe reaction mixture was then cooled to room temperature
8. 8
   Другоеquenched by dropwise addition of water
9. 9
   workup.ADDITIONbefore being diluted with ethyl acetate
10. 10
    ПромывкаThe mixture was then washed with saturated brine
11. 11
    ДругоеThe phases were separated
12. 12
    Сушкаthe organic phase was dried over Na2SO4
13. 13
    Фильтрацияfiltered
14. 14
    Концентрированиеconcentrated in vacuo
15. 15
    ДругоеThe residue was purified by flash chromatography (silica gel, toluene/heptane gradient)

Методика

This compound was prepared using methodology described in Synthesis 1999, 2138-2144. A solution of cyclopropylmagnesium bromide was first prepared by dropwise addition of a solution of 4.06 ml (50.7 mmol) cyclopropyl bromide in 20 ml diethyl ether to 1.23 g (50.7 mmol) magnesium turnings followed by heating at reflux for 5 min. Meanwhile, to a solution of 2.50 g (12.7 mmol) butyl-[1-(2,6-difluoro-phenyl)-meth-(E)-ylidene]-amine in 15 ml ether at 0° C. was added 0.16 g (1.27 mmol) manganese(II) chloride. The freshly prepared solution of cyclopropylmagnesium bromide in diethyl ether was then added dropwise while the temperature of the reaction mixture was maintained at 5-10° C. After the addition was complete, the reaction mixture was stirred for 30 minutes at room temperature and then for 90 minutes at reflux. The reaction mixture was then cooled to room temperature and quenched by dropwise addition of water before being diluted with ethyl acetate. The mixture was then washed with saturated brine. The phases were separated and the organic phase was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, toluene/heptane gradient) to afford 1.51 g (64%) of the title compound as a yellow oil. MS (EI): 158.1 ([M-CO]+, 100%).157.1 ([M-CHO]+., 25%), 129.2 ([M-CHO—C2H4]+., 90%), 115.1 ([M-CHO—C3H6]+., 43%).

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