A kind of synthetic method of pharmaceutical intermediate diaryl substituted ethanol compound
A synthesis method and compound technology, which is applied in the synthesis of diaryl-substituted ethanol compounds as pharmaceutical intermediates, and in the field of synthesis of alcohol compounds, can solve the problems of simple substrates and low yields, and achieve expanded scope and good application prospects and research value effects
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Embodiment 1
[0037]
[0038] At room temperature, add 100mmol of the above formula (I) compound, 150mmol of the above formula (II) compound, 0.5mmol catalyst tris (triphenylphosphine) rhodium chloride (Rh(PPh) to an appropriate amount of solvent tetrahydrofuran 3 ) 3 Cl), 150mmol alkali sodium carbonate, then stir and heat up to 100°C under sealing, and stir and react at this temperature for 8 hours;
[0039] After the reaction, the reaction system was concentrated under reduced pressure to remove the solvent, and the residue was chromatographed on a 300-400 mesh silica gel column, washed with a mixture of petroleum ether and ethyl acetate with a volume ratio of 8:1, and the eluent was collected. The eluting solvent was removed under reduced pressure to obtain the compound of the above formula (III) in a yield of 84.3%.
[0040] NMR: 1 H NMR (500MHz, CDCl 3 )δ2.00 (s, 1H), 2.95-3.05 (m, 2H), 4.86-4.89 (m, 1H), 7.18-7.35 (m, 10H).
Embodiment 2
[0042]
[0043] At room temperature, add 100mmol of the above formula (I) compound, 200mmol of the above formula (II) compound, 1mmol catalyst tris (triphenylphosphine) rhodium chloride (Rh(PPh) to an appropriate amount of solvent tetrahydrofuran 3 ) 3 Cl), 200mmol alkali sodium carbonate, then stir and heat up to 110°C under sealing, and stir and react at this temperature for 6 hours;
[0044] After the reaction, the reaction system was concentrated under reduced pressure, the solvent was removed, the residue was chromatographed on a 300-400 mesh silica gel column, rinsed with a mixture of petroleum ether and ethyl acetate with a volume ratio of 9:1, and the eluent was collected. The eluting solvent was removed under reduced pressure to obtain the compound of the above formula (III) in a yield of 75.8%.
[0045] NMR: 1 H NMR (500MHz, CDCl 3 )δ1.95(s, 1H), 2.25(s, 3H), 2.88-3.00(m, 2H), 5.06-5.09(m, 1H), 7.09-7.30(m, 8H), 7.52(d, J= 7.4Hz, 1H).
Embodiment 3
[0047]
[0048] At room temperature, add 100mmol of the above formula (I) compound, 250mmol of the above formula (II) compound, 1.5mmol catalyst tris (triphenylphosphine) rhodium chloride (Rh(PPh) to an appropriate amount of solvent tetrahydrofuran 3 ) 3 Cl), 250mmol alkali sodium carbonate, then stir and heat up to 120°C under sealing, and stir and react at this temperature for 4 hours;
[0049] After the reaction, the reaction system was concentrated under reduced pressure to remove the solvent, and the residue was chromatographed on a 300-400 mesh silica gel column, washed with a mixture of petroleum ether and ethyl acetate with a volume ratio of 10:1, and the eluent was collected. The eluting solvent was removed under reduced pressure to obtain the compound of the above formula (III) in a yield of 74.5%.
[0050] NMR: 1 H NMR (500MHz, CDCl 3 )δ2.19(s,1H),2.99-3.03(m,1H),3.20-3.24(m,1H),5.58-5.60(m,1H),7.17-7.30(m,5H),7.41-7.52( m,3H),7.61(d,J=7.1Hz,1H),7.75(d,J=8.2H...
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