Method for synthesizing exocyclic enol compound
A technology for exocyclic allenols and compounds, which is applied in the field of synthesizing exocyclic allenol compounds, can solve the problems of insufficient types of allenes, limited substrates, etc., and achieves mild conditions, good substrate applicability, and raw materials. easy-to-get effect
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Embodiment 1
[0021] Synthesis of (3aa):
[0022]
[0023] Add 1a (0.2mmol, 40mg), 2a (0.3mmol, 54mg), rhodium acetate (2.6mg, 2mol%) and n-hexane (2mL) into the reaction tube under the protection of argon; then react at room temperature for 12 hours. Then, 0.8 g of magnesium oxide and dichloromethane (5.0 mL) were added to the reaction flask, and the reaction was continued at 40 degrees Celsius for 3 hours, then filtered through diatomaceous earth to remove the filter residue of magnesium oxide, and the filtrate was concentrated under reduced pressure to obtain a crude product, which was passed through Purified by column chromatography to obtain (3aa) (49.6mg, dr>19:1, yield: 79%) as a light yellow solid. The melting point is 165-168°C, 1 H NMR (400MHz, CDCl3) δ7.47-7.42(m,2H),7.34-7.25(m,3H),7.20-7.17(m,3H),6.94-6.92(m,2H),6.86(s,1H ),3.23(s,1H),2.58-2.34(m,2H),2.17(s,3H),1.16(t,J=7.6Hz,3H). 13 C NMR (100MHz, CDCl3) δ204.0, 202.9, 162.4, 141.3, 141.1, 132.8, 128.7, 128.5, 128.0, 127....
Embodiment 2
[0025] Synthesis of (3ab):
[0026]
[0027] Add 1a (0.2mmol, 40mg), 2b (0.3mmol, 58mg), rhodium acetate (2.6mg, 2mol%) and n-hexane (2mL) into the reaction tube under the protection of argon; then react at room temperature for 12 hours. Then, 0.8 g of magnesium oxide and dichloromethane (5 mL) were added to the reaction flask, and the reaction was continued at 40 degrees Celsius for 3 hours, then filtered through diatomaceous earth to remove the filter residue of magnesium oxide, and the filtrate was concentrated under reduced pressure to obtain the crude product, which was passed through the column Purified by chromatography to obtain (3ab) (50.6mg, dr>19:1, yield: 76%) as a light yellow solid with a melting point of 126-128°C, 1 H NMR (400MHz, CDCl 3 )δ7.31(d, J=8.0Hz, 2H), 7.19-7.16(m, 3H), 7.09(d, J=8.0Hz, 2H), 6.99-6.94(m, 2H), 6.83(s, 1H ),3.18(s,1H),2.52-2.36(m,2H),2.30(s,3H),2.13(s,3H),1.12(t,J=7.6Hz,3H). 13 C NMR (100MHz, CDCl 3 C 23 h 23 o 2 [M+H] + :331....
Embodiment 3
[0029] Synthesis of (3ac):
[0030]
[0031] Add 1a (0.2mmol, 40mg), 2c (0.3mmol, 64mg), rhodium acetate (2.6mg, 2mol%) and n-hexane (2mL) into the reaction tube under the protection of argon; then react at room temperature for 12 hours. Then, 0.8 g of magnesium oxide and dichloromethane (5 mL) were added to the reaction flask, and the reaction was continued at 40 degrees Celsius for 3 hours, then filtered through diatomaceous earth to remove the filter residue of magnesium oxide, and the filtrate was concentrated under reduced pressure to obtain the crude product, which was passed through the column Purified by chromatography to obtain (3ac) (42.3mg, dr>19:1, yield: 76%) as an oily liquid,1 H NMR (400MHz, CDCl 3 )δ8.36(d, J=2.4Hz, 1H), 7.82(dd, J=8.4, 2.4Hz, 1H), 7.26-7.20(m, 4H), 7.06-6.96(m, 2H), 6.90(s ,1H),3.33(s,1H),2.51-2.32(m,2H),2.18(s,3H),1.11(t,J=7.6Hz,3H). 13 C NMR (75MHz, CDCl 3 )δ202.7,202.4,162.9,151.2,146.7,141.0,136.6,136.0,132.0,129.1,128.5,127.2,124.2,...
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