反应详情

To a stirred solution of 4-methyl-5-imidazolemethanol (587 mg, 3.96 mmol) in anhydrous DMF (13 mL) was added DIPEA (2.1 mL, 11.9 mmol) followed by 2-(trimethylsilyl)ethoxymethyl chloride (793 mg, 4.76 mmol). The resultant solution was heated to 80° C. for 3 h then cooled to room temperature. The reaction mixture was poured into brine (15 mL), and diluted with H2O (6 mL) and EtOAc (40 mL). The phases were mixed vigorously for 10 minutes and separated. The organic phase was washed with brine (4×20 mL), dried (Na2SO4), and concentrated under reduced pressure. Purification of the crude orange oil by flash chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 95:4:1) provided [5-Methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-4-yl]-methanol (535 mg, 56%) as a mixture of regioisomers.

1. additionThe phases were mixed vigorously for 10 minutes
2. customseparated
3. washThe organic phase was washed with brine (4×20 mL)
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated under reduced pressure
6. customPurification of the crude orange oil by flash chromatography on silica gel (CH2Cl2/MeOH/NH4OH, 95:4:1)