(E)-3-(氧杂-4-基)丙-2-烯腈

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

实验步骤: To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.25 g, 0.00644 mol) in acetonitrile (20 mL, 0.4 mol) was added (2E)-3-(tetrahydro-2H-pyran-4-yl)acrylonitrile (1.00 g, 0.00729 mol), followed by 1,8-diazabicyclo[5.4.0]undec-7-ene (1.09 mL, 0.00729 mol). The resulting mixture was stirred at room temperature overnight. After being evaporated to dryness, the residue was purified on silica gel, eluting with 0-100% EtOAc in hexanes, to provide the desired product (1.30 g, 60.93%). LCMS (M+H) 332.4. After being evaporated to dryness the residue was purified on silica gel eluting with 0-100% EtOAc in hexanes

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

实验步骤: To a solution of 1.0 M of potassium tert-butoxide in tetrahydrofuran (9.20 mL, 0.00920 mol) at 0° C. was added dropwise a solution of diethyl cyanomethylphosphonate (1.56 mL, 0.00965 mol) in tetrahydrofuran (11.73 mL, 0.1447 mol). The reaction was warmed to room temperature and then cooled at 0° C. again. To the reaction mixture was added a solution of tetrahydro-2H-pyran-4-carbaldehyde (1.0 g, 0.0088 mol) in tetrahydrofuran (2.35 mL, 0.0289 mol). The reaction was allowed to warm up to room temperature and stirred overnight. After being quenched with water, the mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried and evaporated to dryness. The crude mixture was used directly in next step. LCMS (M+H) 138.0. cooled at 0° C. again to warm up to room temperature After being quenched with water the mixture was extracted with EtOAc The combined organic layers were washed with brine dried evaporated to dryness