2-tert-butylbenzaldehyde

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of (5Z)-5-(piperidin-4-ylmethylidene)-4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one dihydrochloride (200 mg) in DMF (2 mL) was added a solution of triethylamine (0.35 mL) and 2-tert-butylbenzaldehyde (101 mg) in DMF (1 mL). The reaction mixture was stirred at room temperature for 1 hr, and sodium triacetoxyborohydride (554 mg) was added. The reaction mixture was stirred at room temperature overnight, saturated aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (92 mg). The reaction mixture was stirred at room temperature overnight the mixture was extracted with ethyl acetate The extract was washed with water and saturated brine dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure The residue was purified by silica gel column chromatography (ethyl acetate/hexane) recrystallized from ethyl acetate/heptane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of (2-tert-butylphenyl)methanol (935 mg) in DMSO (20 mL) were added triethylamine (4.81 mL) and sulfur trioxide pyridine complex (3.02 g). The reaction mixture was stirred at room temperature for 1 hr, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (780 mg). the mixture was extracted with ethyl acetate The extract was washed with water and saturated brine dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure The residue was purified by silica gel column chromatography (ethyl acetate/hexane)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: After 3 ml of tetrahydrofuran was cooled to −10° C., 0.91 ml of n-butyllithium (2.6 M hexane solution) and 1.35 ml of n-butylmagnesium chloride (0.91 M tetrahydrofuran solution) were added. After 30 minutes of stirring, 0.98 g of 8-fluoro-3-iodoquinoline was added and the mixture was stirred for 15 minutes. 0.49 g of 2-t-butylbenzaldehyde was added to the reaction solution and the mixture was stirred for 3 hours. After dilute hydrochloric acid was added to the reaction mixture, the liquid was separated with ethyl acetate. After the organic layer was concentrated and purified by silica gel column chromatography, 0.55 g of (2-t-butyl-phenyl)-(8-fluoro-quinolin-3-yl)-methanol (Compound Number 54) was obtained. the mixture was stirred for 15 minutes the mixture was stirred for 3 hours the liquid was separated with ethyl acetate After the organic layer was concentrated purified by silica gel column chromatography