2-hydroxyethyl acetate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 7.95 g (31.3 mmol) of methyl 3,3-diphenyl-2,3-epoxypropionate were dissolved in 20 ml of diethyl ether under N2 and cooled to 0° C., and 5.87 ml (31.3 mmol) of 2-hydroxyethyl acetate (50% strength) and 3 drops of BF3.Et2O were added. After removal of the ice bath, the mixture was stirred at RT for 2 h. After removal of the ice bath

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a soln. of 2-(bromomethyl)-4,6-dichlorobenzonitrile (1.3 mmol) (A.2.2.1.) and 2-hydroxyethyl acetate (1.43 mmol) in 7 mL THF was added NaH (1.95 mmol, 60% suspension in oil). The reaction mixture was stirred at RT overnight and then poured into a 1M HCl soln. The mixture was extracted twice with EtOAc. The comb. org. layers were washed with brine, dried over MgSO4 and conc. in vacuo. Purification with CC (0-25% EtOAc/Hept) gives the desired compound as orange oil. The mixture was extracted twice with EtOAc layers were washed with brine dried over MgSO4 and conc. in vacuo Purification with CC (0-25% EtOAc/Hept)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 7.95 g (31.3 mmol) of methyl 3,3-diphenyl-2,3-epoxypropionate were dissolved in 20 ml of diethyl ether under N2 and cooled to 0° C., and 5.87 ml (31.3 mmol) of 2-hydroxyethyl acetate (50% strength) and 3 drops of BF3.Et2O were added. After removal of the ice bath, the mixture was stirred at RT for 2 h. After removal of the ice bath

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In an atmosphere of nitrogen, a mixture of 2-hydroxyethyl acetate, sodium hydride and DMF was stirred at room temperature for 15 minutes and then 1-bromo-4-fluoro-2-(trifluoromethyl)benzene was added, followed by stirring at room temperature for 1.5 hours to obtain 2-[4-bromo-3-(trifluoromethyl)phenoxy]ethanol. by stirring at room temperature for 1.5 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In an atmosphere of nitrogen, a mixture of 2-hydroxyethyl acetate, sodium hydride and DMF was stirred at room temperature for 15 minutes and then 1-bromo-4-fluoro-2-(trifluoromethyl)benzene was added, followed by stirring at room temperature for 1.5 hours to obtain 2-[4-bromo-3-(trifluoromethyl)phenoxy]ethanol. by stirring at room temperature for 1.5 hours

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Commercially available 2-hydroxyethyl acetate (3.12 g, 30.0 mmol), triethylamine (4.6 ml, 33 mmol), and 4-(N,N-dimethylamino)pyridine (100 mg) were dissolved in dichloromethane (20 ml), then tert-butylchlorodiphenylsilane (8.65 g, 31.5 mmol) was added thereto at room temperature, and the mixture was stirred for 20 hours. The obtained solution was diluted with a mixed solvent of hexane-ethyl acetate (1:1), and then the resulting solution was washed with water and with an aqueous solution of sodium chloride. The solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was dissolved in methanol (100 ml), and 28% sodium methoxide in methanol (3 ml) was added thereto at room temperature followed by stirring for 2 hours. The solvent was distilled off under reduced pressure, and the residue was partitioned between ethyl acetate and a phosphate buffer solution (pH 7), then the organic layer was washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to afford the crude title compound (5.18 g, 57% gross yield) as a colorless oil. the resulting solution was washed with water and with an aqueous solution of sodium chloride The solution was dried over anhydrous magnesium sulfate the solvent was distilled off under reduced pressure The residue was dissolved in methanol (100 ml) 28% sodium methoxide in methanol (3 ml) was added at room temperature by stirring for 2 hours The solvent was distilled off under reduced pressure the residue was partitioned between ethyl acetate a phosphate buffer solution (pH 7), then the organic layer was washed with an aqueous solution of sodium chloride dried over anhydrous magnesium sulfate The solvent was distilled off under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-(4-Fluorophenyl)-2-(4-hydroxyphenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide, 2-hydroxyethyl acetate, triphenylphosphine and diethylazodicarboxylate are reacted and treated in the same manner as in Example 24 to give 2-(4-(2-acetoxyethyloxy)phenyl)-5-(4-fluorophenyl)-N-(2-thiazolyl)imidazole-4-carboxamide. treated in the same manner as in Example 24

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-(4-Chlorophenyl)-2-(4-hydroxyphenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide, 2-hydroxyethyl acetate, triphenylphosphine and diethyl azodicarboxylate are reacted and treated in the same manner as in Example 24 to give 2-(4-(2-acetoxyethyloxy)phenyl)-5-(4-chlorophenyl)-N-(2-thiazolyl)imidazole-4-carboxamide. treated in the same manner as in Example 24

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-(4-Hydroxyphenyl)-5-(4-methoxyphenyl)-N-(2-thiazolyl)-imidazole-4-carboxamide, 2-hydroxyethyl acetate, triphenylphosphine and diethyl azodicarboxylate are reacted and treated in the same manner as in Example 24 to give 2-(4-(2-acetoxyethyloxy)phenyl)-5-(4-methoxyphenyl)-N-(2-thiazolyl)imidazole-4-carboxamide. treated in the same manner as in Example 24