1-(diethoxymethyl)-1H-imidazole → Rac-(2-chloro-6-ethyl-phenyl)-(1h-imidazol-2-yl)-methanol

Temperature

0 °C

To a solution of 1.60 ml (9.79 mmol) 1-(diethoxymethyl)imidazole in 6 ml tetrahydrofuran at −78° C. was added dropwise 6.67 ml (10.7 mmol) of a 1.6 M solution of n-butyllithium in hexane. The resulting solution of 2-(1-diethoxymethyl-1H-imidazol-2-yl)-lithium was stirred at −78° C., and then added dropwise to a solution of 1.50 g (8.90 mmol) 2-chloro-6-ethyl-benzaldehyde in 6 ml tetrahydrofuran at 0° C. The reaction mixture was then stirred at 0° C. for 30 min and at room temperature for 1 h, before being quenched by dropwise addition of 1 M aqueous hydrochloric acid. The mixture was made basic by addition of aqueous sodium bicarbonbate solution and diluted with ethyl acetate. The phases were separated and the organic phase was washed with saturated brine, dried over Na2SO4, filtered and concentrated in vacuo to afford 2.02 g (96%) of the title compound as a yellow oil which was used in the next step without further purification.

1. custombefore being quenched by dropwise addition of 1 M aqueous hydrochloric acid
2. additionThe mixture was made basic by addition of aqueous sodium bicarbonbate solution
3. additiondiluted with ethyl acetate
4. customThe phases were separated
5. washthe organic phase was washed with saturated brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-fb0ff5af83ff4a84b6de1cbebac26022

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07875645B2