Tetrahydrofuran → 2-Ethyl-6-methylbenzaldehyde

Temperature

7.5 °C

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).

1. customThis compound was prepared
2. customdescribed in Synthesis 1999, 2138-2144
3. additionAfter the addition
4. customrose to 50° C.
5. customThe reaction mixture was then quenched by dropwise addition of water
6. additionbefore being diluted with ethyl acetate
7. washThe mixture was then washed sequentially with water and with saturated brine
8. customThe phases were separated
9. dry with materialthe organic phase was dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThe residue was purified by flash chromatography (silica gel, ethyl acetate/heptane gradient)

ORD record

ord-0376661e376842659bbf6ffccfcb1d4e

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08158668B2