4-氯-3-甲氧基苯酚

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a mixture of 2-chloromethyl-1-(3,5-dichlorobenzyl)-1H-imidazole hydrochloride (see Example 1) (150 mg, 0.5 mmol), 4-chloro-3-methoxyphenol (158 mg, 1 mmol) and DMSO (1 mL) was added K2CO3 (415 mg, 3 mmol). The reaction was stirred at ambient temperature for 8 h before diluting with water (10 mL). A solution of 1N HCl was added until the mixture was only slightly basic (pH 8) before extracting with EtOAc (30 mL). The EtOAc phase was washed with water (10 mL), dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 1:2, hexanes/EtOAc) to afford the title compound (194 mg, 97%) as a white solid: ESI MS m/z 397 [C18H15Cl3N2O2+H]+. before extracting with EtOAc (30 mL) The EtOAc phase was washed with water (10 mL) dried (Na2SO4) concentrated in vacuo The residue was purified by column chromatography (silica gel, 1:2, hexanes/EtOAc)

反应条件: temp:23.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 1.0 g (6.3 mmol) 4-chloro-3-methoxyphenol and 5.4 g (6.3 mmol) crotonic acid in 15 ml methane sulfonic acid was heated at 95° C. under nitrogen for 20 hours. The reaction was cooled to 23° C., poured onto 150 ml ice and water and extracted with 100 ml ethyl acetate. The ethyl acetate extract was successively washed with 100 ml water, 2×100 ml 1N sodium hydroxide and 100 ml brine, dried over magnesium sulfate and concentrated in vacuo to a purple crystalline solid. This was purified by flash chromatography on 150 cc silica gel using chloroform as eluant to give the product as a yellow crystalline solid, 1.1 g (78%); m.p. 96°-100° C. extracted with 100 ml ethyl acetate The ethyl acetate extract was successively washed with 100 ml water, 2×100 ml 1N sodium hydroxide and 100 ml brine dried over magnesium sulfate concentrated in vacuo to a purple crystalline solid This was purified by flash chromatography on 150 cc silica gel