Diethyl Ether → 2-Cyclopropyl-6-methyl-benzaldehyde

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence