Tetrahydrofuran → 2-Ethyl-6-methylbenzaldehyde

Participants

Reaction Conditions

Reaction Steps

This compound was prepared using methodology described in Synthesis 1999, 2138-2144. 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. 15.3 ml (30.5 mmol) of a 2 M solution of ethylmagnesium chloride 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 a further 90 minutes, during which time the temperature rose to 50° C. (exotherm). The reaction mixture was then 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 1.88 g (83%) of the title compound as a yellow oil. 1H-NMR (CDCl3): 1.26 (3H, t, CH3), 2.60 (3H, s, CH3), 2.98 (2H, q, CH2), 7.09 (1H, d, ArH), 7.12 (1H, d, ArH), 7.35 (1H, dd, ArH), 10.6 (1H, s, CHO).

Provenance & Evidence