تفاعل #166175

معادلة التفاعل

sodium tert-butoxide

phosphine

4-chlorotoluene

morpholine

→

4-Tolylmorpholine

المذيبات

acetonitrile

CH2Cl2

dioxane

ظروف التفاعل

المعالجة

1. 1
   أخرىIn a nitrogen-atmosphere glovebox, a microwave vial equipped with a magnetic stir bar
2. 2
   أخرىThe vial was sealed with a crimp top
3. 3
   أخرىthe vial was removed from the heating block
4. 4
   درجة الحرارةcooled to room temperature
5. 5
   أخرىreaction
6. 6
   ترشيحfiltering into a round-bottom flask
7. 7
   غسيلThe vial was rinsed with CH2Cl2 (5 mL)
8. 8
   غسيلby washing of the filter cake with CH2Cl2 (2 mL)
9. 9
   أخرىThe volatiles were removed on a rotary evaporator
10. 10
    تركيزthe crude concentrate
11. 11
    أخرىwas purified by silica gel column chromatography (25 g silica gel, 85:15 heptane:ethyl acetate)
12. 12
    أخرىThe purified product was isolated as a beige solid

الإجراء التجريبي

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).

المصدر