1-苯基氮杂-2-one

反应条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 1-Phenylazepan-2-one (0.500 g, as prepared in Organic Letters 2000, pages 1101-1104) was dissolved in tetrahydrofuran (30 mL) and cooled to −78° C. To the solution was added LDA (2.0 mol/L in THF/heptane/ethylbenzene, 2.6 mL) dropwise. After stirring for 10 min between −55 and −50° C., the reaction mixture was warmed up to −40° C., stirred for 5 min and ethylformate (0.657 mL, 0.605 g) was added slowly. The mixture was warmed up to 0° C. and stirred for another 30 min. 2-Chloro-4-methyl-2H-furan-5-one (0.420 g in 2 mL of THF) was added dropwise. The reaction mixture was warmed up to room temperature and stirred for 3 h. Water and ethyl acetate were added and the layers were separated. The aqueous layer was extracted with ethyl acetate, the organic layers were combined, washed with water and brine, dried over Na2SO4 and the solvent was evaporated to give a brown residue which was purified by flash chromatography (0-100% ethyl acetate in cyclohexane). (3E)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylene]-1-phenyl-azepan-2-one Ic-13 (0.103 g, 11%) was obtained as a white solid; mp: 150-160° C.; LCMS (Method D): 0.91 min; ES+314 (M+H+). the reaction mixture was warmed up to −40° C. stirred for 5 min The mixture was warmed up to 0° C. stirred for another 30 min The reaction mixture was warmed up to room temperature stirred for 3 h the layers were separated The aqueous layer was extracted with ethyl acetate washed with water and brine dried over Na2SO4 the solvent was evaporated to give a brown residue which was purified by flash chromatography (0-100% ethyl acetate in cyclohexane)

反应条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 1-Phenylazepan-2-one (0.500 g, as prepared in Organic Letters 2000, pages 1101-1104) was dissolved in tetrahydrofuran (30 mL) and cooled to −78° C. To the solution was added LDA (2.0 mol/L in THF/heptane/ethylbenzene, 2.6 mL) dropwise. After stirring for 10 min between −55 and −50° C., the reaction mixture was warmed up to −40° C., stirred for 5 min and ethylformate (0.657 mL, 0.605 g) was added slowly. The mixture was warmed up to 0° C. and stirred for another 30 min. 2-Chloro-4-methyl-2H-furan-5-one (0.420 g in 2 mL of THF) was added dropwise. The reaction mixture was warmed up to room temperature and stirred for 3 h. Water and ethyl acetate were added and the layers were separated. The aqueous layer was extracted with ethyl acetate, the organic layers were combined, washed with water and brine, dried over Na2SO4 and the solvent was evaporated to give a brown residue which was purified by flash chromatography (0-100% ethyl acetate in cyclohexane). (3E)-3-[(4-methyl-5-oxo-2H-furan-2-yl)oxymethylene]-1-phenyl-azepan-2-one Ic-13 (0.103 g, 11%) was obtained as a white solid; mp: 150-160° C.; LCMS (Method D): 0.91 min; ES+314 (M+H+). the reaction mixture was warmed up to −40° C. stirred for 5 min The mixture was warmed up to 0° C. stirred for another 30 min The reaction mixture was warmed up to room temperature stirred for 3 h the layers were separated The aqueous layer was extracted with ethyl acetate washed with water and brine dried over Na2SO4 the solvent was evaporated to give a brown residue which was purified by flash chromatography (0-100% ethyl acetate in cyclohexane)