A kind of alkenylated product of allyl alcohol urethane compound and its synthetic method
A technology of allyl alcohol urethane formic acid and ester compounds, which is applied in the preparation of organic compounds, steroids, organic chemical methods, etc., and achieves the effects of wide application prospects, mild reaction conditions, and simple operation
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Embodiment 1
[0035]
[0036] Palladium acetate (4.5 mg, 10 mol%, 0.02 mmol), N-acetylglycine (4.7 mg, 20 mol%, 0.04 mmol), silver carbonate (165.5 mg, 3.0 eq, 0.6 mmol) was charged to an oven-dried screw cap vial and trifluoroethanol (1.0 mL). Then, the corresponding carbamate (0.2 mmol, 1.0 equiv) and the corresponding alkene (0.40 mmol, 2.0 equiv) were sequentially added to the solution. The vial was sealed under nitrogen and heated to 80°C and stirred for 16 hours. After cooling, the mixture was filtered and concentrated to give the crude product, which was directly applied to flash column chromatography (ethyl acetate / petroleum ether mixture) to give bright yellow liquid (33.3 mg, yield 56%).
[0037] The NMR spectrum peaks are as follows: 1 H NMR (CDCl 3 ):δ=7.20(d,J=16.0Hz,1H),6.05(t,J=7.5Hz,1H),5.91(d,J=16.0Hz,1H),4.73(s,2H),4.09(t ,J=7.0Hz,2H),2.85(brs,3H),2.78(brs,3H),2.22-2.27(m,2H),1.56-1.61(m,2H),1.30-1.44(m,4H), 0.85-0.89(m,6H). 13 C NMR (CDCl 3): δ=166.52, 155.31, 1...
Embodiment 2
[0039]
[0040] Palladium acetate (4.5 mg, 10 mol%, 0.02 mmol), N-acetylglycine (4.7 mg, 20 mol%, 0.04 mmol), silver carbonate (165.5 mg, 3.0 eq, 0.6 mmol) was charged to an oven-dried screw cap vial and trifluoroethanol (1.0 mL). Then, the corresponding carbamate (0.2 mmol, 1.0 equiv) and the corresponding alkene (0.40 mmol, 2.0 equiv) were sequentially added to the solution. The vial was sealed under nitrogen and heated to 80°C and stirred for 16 hours. After cooling, the mixture was filtered and concentrated to give the crude product, which was directly applied to flash column chromatography (ethyl acetate / petroleum ether mixture) to give a bright yellow liquid (33.0 mg, 45% yield).
[0041] The NMR spectrum peaks are as follows: 1 H NMR (CDCl 3 ): δ=7.22(d, J=16.0Hz, 1H), 6.06(t, J=7.6Hz, 1H), 5.92(d, J=16.0Hz, 1H), 4.73(s, 2H), 3.68(s ,3H),2.85(brs,3H),2.78(brs,3H),2.22-2.28(m,2H),1.37-1.43(m,2H),0.86(t,J=7.6Hz,3H). 13 C NMR (CDCl 3 ): δ=167.85, 156.29, 146.96, 1...
Embodiment 3
[0043]
[0044] Palladium acetate (4.5 mg, 10 mol%, 0.02 mmol), N-acetylglycine (4.7 mg, 20 mol%, 0.04 mmol), silver carbonate (165.5 mg, 3.0 eq, 0.6 mmol) was charged to an oven-dried screw cap vial and trifluoroethanol (1.0 mL). Then, the corresponding carbamate (0.2 mmol, 1.0 equiv) and the corresponding alkene (0.40 mmol, 2.0 equiv) were sequentially added to the solution. The vial was sealed under nitrogen and heated to 80°C and stirred for 16 hours. After cooling, the mixture was filtered and concentrated to give the crude product, which was directly applied to flash column chromatography (ethyl acetate / petroleum ether mixture) to give a bright yellow liquid (24.8 mg, 46% yield).
[0045] The NMR spectrum peaks are as follows: 1 H NMR (CDCl 3 ): δ=7.21(d, J=16.0Hz, 1H), 6.06(t, J=7.6Hz, 1H), 5.91(d, J=16.0Hz, 1H), 4.73(s, 2H), 4.14(q ,J=7.2Hz,2H),2.85(brs,3H),2.78(brs,3H),2.22-2.27(m,2H),1.37-1.43(m,2H),1.23(t,J=7.2Hz, 3H), 0.86(t, J=7.2Hz, 3H). 13 C NMR (CDCl ...
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