Ethyl Acetate → HCID 53697912, compound

Temperature

-20 °C

A stirred suspension containing [(4-methoxyphenyl)methyl]triphenylphosphonium bromide (8.3 g, 0.020 mol) in dry tetrahydrofuran (50 ml) at -20° C. under a nitrogen atmosphere was treated with a solution containing n-butyl lithium (14.3 ml of 1.4M; 0.020 mol) in hexane. The resulting deep-red solution was stirred at -20° C. for 20 minutes and was allowed to warm to room temperature. Stirring was maintained for an additional 20 minutes and the solution was cooled to -20° C. The cooled solution was treated with a solution of 1-(1H-imidazol-1-yl)-3-[(4-methoxyphenyl)methoxy]-2-propanone (Example 1c; 2.6 g, 0.010 mol) in dry tetrahydrofuran (20 ml) and the resulting mixture was stirred at room temperature for 14 hours. Ethyl acetate (500 ml) was added to the mixture and the resulting mixture was washed with water (3×150 ml) and dried over sodium sulfate. The solvent was evaporated off under reduced pressure to yield a crude product which was purified by column chromatography (silica gel, 30% hexane in chloroform) to give an isomeric mixture of E- and Z-1-[3-(4-methoxyphenyl)-2-[[(4-methoxyphenyl)methoxy]methyl]-2-propenyl]-1H-imidazole as a pale-yellow oil having the following structural characteristics:

1. additionwas treated with a solution
2. temperatureto warm to room temperature
3. stirringStirring
4. temperaturewas maintained for an additional 20 minutes
5. temperaturethe solution was cooled to -20° C
6. stirringthe resulting mixture was stirred at room temperature for 14 hours
7. washthe resulting mixture was washed with water (3×150 ml)
8. dry with materialdried over sodium sulfate
9. customThe solvent was evaporated off under reduced pressure

ORD record

ord-a601e5fcfebd4af2a4d6ae842ec308d8

Source dataset

uspto-grants-1989_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04837333