Method for preparing novel vinyl silicon compound
A technology of vinyl silicon and compounds, which is applied in the field of preparation of new vinyl silicon compounds, can solve the problems of β-type vinyl silicon compounds that have not been reported publicly, and achieve mild reaction conditions and high reaction efficiency Effect
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Embodiment 1
[0021] Example 1: Preparation of (Z)-3(2-phenyl-2-(triethylsilyl)vinyl)oxazolidin-2-one
[0022] Under nitrogen, 3-phenylethynyl-pyrazolin 2-one (0.2mmol, 37.4mg) was dissolved in acetonitrile (2mL), then triethylsilane (0.4mmol, 46.4mg) and [Rh( CO) 2 Cl] 2 (0.005mmol, 1.9mg), the reaction mixture was stirred at room temperature, and reacted for 12h. After the reaction, column chromatography separated to obtain 46.1mg of a yellow oily product, Z / E=15:1, and the yield was 76%.
[0023]
[0024] 1 H NMR (400MHz, CDCl 3 ,TMS):δ7.29-7.25(m,2H),7.22-7.20(m,1H),7.11-7.08(m,2H),6.65(s,1H),4.42(t,J=8.0Hz,2H ), 3.85(t, J=8.0Hz, 2H), 0.92(t, J=8.0Hz, 9H), 0.65(q, J=8.0Hz, 6H). 13 C NMR (125MHz, CDCl 3 ): δ157.4, 143.7, 136.7, 136.0, 128.0, 128.0, 126.0, 62.1, 47.4, 7.6, 4.4. -1 .HRMS(EI-TOF)m / z:[M] + Calcd for C 17 h 25 NO 2 Si 303.1655; Found 303.1664.
Embodiment 2
[0025] Example 2: Preparation of (Z)-3(2-(4-methoxyphenyl)-2-(triethylsilyl)vinyl)oxazolidin-2-one
[0026] Under nitrogen, 3-p-methoxyphenylethynyl-pyrazolin 2-one (0.2 mmol, 43.4 mg) was dissolved in acetonitrile (2 mL) and triethylsilane (0.4 mmol, 46.4 mg) was added and [Rh(CO) 2 Cl] 2 (0.005mmol, 1.9mg), the reaction mixture was stirred at room temperature, and reacted for 12h. After the reaction, column chromatography separated to obtain 46.6mg of yellow oily product, Z / E>20:1, and the yield was 70%.
[0027]
[0028] 1 H NMR (500MHz, CDCl 3 , TMS): δ7.02(d, J=10.0Hz, 2H), 6.81(d, J=10.0Hz, 2H), 6.60(s, 1H), 4.41(t, J=10.0Hz, 2H), 3.82 (t,J=10.0Hz,2H),3.80(s,3H),0.92(t,J=10.0Hz,9H),0.65(q,J=10.0Hz,6H). 13 C NMR (125MHz, CDCl 3 ): δ158.0, 157.5, 136.6, 135.9, 129.8, 129.0, 113.4, 62.1, 56.2, 47.5, 7.6, 4.3. -1 .HRMS(EI-TOF)m / z:[M] + Calcd for C 18 h 27 NO 3 Si 333.1760; Found 333.1764.
Embodiment 3
[0029] Example 3: Preparation of (Z)-3(2-(4-chlorophenyl)-2-(triethylsilyl)vinyl)oxazolidin-2-one
[0030] Under nitrogen, 3-p-chlorophenylethynyl-pyrazolin 2-one (0.2 mmol, 44.2 mg) was dissolved in acetonitrile (2 mL), and triethylsilane (0.4 mmol, 46.4 mg) and [ Rh(CO) 2 Cl] 2 (0.005mmol, 1.9mg), the reaction mixture was stirred at room temperature, and reacted for 12h. After the reaction, column chromatography separated to obtain 46.5mg of a yellow oily product, Z / E=18:1, and the yield was 69%.
[0031]
[0032] 1 H NMR (500MHz, CDCl 3 , TMS): δ7.24(d, J=10.0Hz, 2H), 7.02(d, J=10.0Hz, 2H), 6.65(s, 1H), 4.42(t, J=10.0Hz, 2H), 3.85 (t,J=10.0Hz,2H),0.92(t,J=10.0Hz,9H),0.64(q,J=10.0Hz,6H). 13 C NMR (125MHz, CDCl 3 ): δ157.3, 142.3, 137.1, 134.2, 132.0, 129.4, 128.1, 62.1, 47.2, 7.6, 4.4. IR (KBr) ν2957, 2305, 1762, 1481, 1264, 749, 705cm - 1 .HRMS(EI-TOF)m / z:[M] + Calcd for C 17 h 24 ClNO 2 Si 337.1265; Found 337.1257.
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