反応 #166175
ord-8abc60f3d4bd49a891f525287bc03d17
反応条件
後処理
- 1その他In a nitrogen-atmosphere glovebox, a microwave vial equipped with a magnetic stir bar
- 2その他The vial was sealed with a crimp top
- 3その他the vial was removed from the heating block
- 4温度cooled to room temperature
- 5その他reaction
- 6ろ過filtering into a round-bottom flask
- 7洗浄The vial was rinsed with CH2Cl2 (5 mL)
- 8洗浄by washing of the filter cake with CH2Cl2 (2 mL)
- 9その他The volatiles were removed on a rotary evaporator
- 10濃縮the crude concentrate
- 11その他was purified by silica gel column chromatography (25 g silica gel, 85:15 heptane:ethyl acetate)
- 12その他The purified product was isolated as a beige solid
実験手順
In a nitrogen-atmosphere glovebox, a microwave vial equipped with a magnetic stir bar was charged with sodium tert-butoxide (56.9 mg, 0.592 mmol, 1.5 equivalents), tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) (3.62 mg, 0.00395 mmol, 0.01 equivalents), phosphine ligand (0.00869 mmol, 0.022 equivalents) and dioxane (0.79 mL). To the slurry was added 4-chlorotoluene (47 μL, 0.395 mmol, 1 equivalents) and morpholine (42 μL, 0.474 mmol, 1.2 equivalents). The vial was sealed with a crimp top and stirred at 100° C. After 14 hours, the vial was removed from the heating block, cooled to room temperature and brought out of the glovebox. To assay the crude reaction, an aliquot (7 μL) was taken and diluted in acetonitrile (1.5 mL), then injected onto an HPLC instrument. For isolation purposes, the reaction solution was worked up by diluting with CH2Cl2 (2 mL) and filtering into a round-bottom flask. The vial was rinsed with CH2Cl2 (5 mL), followed by washing of the filter cake with CH2Cl2 (2 mL). The volatiles were removed on a rotary evaporator and the crude concentrate was purified by silica gel column chromatography (25 g silica gel, 85:15 heptane:ethyl acetate). The purified product was isolated as a beige solid. 1H NMR (400 MHz, CDCl3) δ ppm 7.10 (d, J=8.2 Hz, 1H), 6.88-6.81 (m, 2H), 3.87 (dd, J=5.7, 3.9 Hz, 4H), 3.15-3.09 (m, 4H), 2.29 (s, 3H).