Reaktion #341733

Reaktionsgleichung

butyl-[1-(2-chloro-6-methyl-phenyl)-meth-(E)-ylidene]-amine

cyclopropylmagnesium bromide

diethyl ether

cyclopropylmagnesium bromide

cyclopropyl bromide

magnesium

diethyl ether

→

title compound

Ausbeute 65.0%

2-Cyclopropyl-6-methyl-benzaldehyde

Ausbeute 65.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThis compound was prepared
2. 2
   Sonstigedescribed in Synthesis 1999, 2138-2144
3. 3
   Temperaturby heating
4. 4
   Temperaturat reflux for 5 min
5. 5
   Sonstigerose to 50° C
6. 6
   workup.ADDITIONAfter the addition
7. 7
   TemperaturThe reaction mixture was then cooled to room temperature
8. 8
   Sonstigequenched by dropwise addition of water
9. 9
   workup.ADDITIONbefore being diluted with ethyl acetate
10. 10
    WaschenThe mixture was then washed sequentially with water and with saturated brine
11. 11
    SonstigeThe phases were separated
12. 12
    Trocknenthe organic phase was dried over Na2SO4
13. 13
    Filtrationfiltered
14. 14
    Einengenconcentrated in vacuo
15. 15
    SonstigeThe residue was purified by flash chromatography (silica gel, ethyl acetate/heptane gradient)

Vorschrift

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 3.06 ml (38.2 mmol) cyclopropyl bromide in 15 ml diethyl ether to 0.93 g (38.2 mmol) magnesium turnings followed by heating at reflux for 5 min. Meanwhile, to a solution of 3.20 g (15.3 mmol) butyl-[1-(2-chloro-6-methyl-phenyl)-meth-(E)-ylidene]-amine in 30 ml tetrahydrofuran at 0° C. was added 0.19 g (1.53 mmol) manganese(II) chloride. The freshly prepared solution of cyclopropylmagnesium bromide in diethyl ether was then added dropwise, during which the temperature of the reaction mixture rose to 50° C. After the addition was complete, the reaction mixture was heated at 60° C. for 16 h. 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 sequentially with water and 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, ethyl acetate/heptane gradient) to afford 1.60 g (65%) of the title compound as a yellow oil. 1H-NMR (CDCl3): 0.75 (2H, m, CH2), 1.04 (2H, m, CH2), 2.39 (1H, m, CH), 2.59 (3H, s, CH3), 7.07 (1H, t, ArH), 7.33 (2H, m, ArH), 10.9 (1H, s, CHO).

Quelle