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A kind of synthetic method of arylmethyl sulfone
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A kind of technology of arylmethyl alkyl sulfone and synthesis method, which is applied in the synthesis field of aryl methyl alkyl sulfone, and can solve problems such as no literature report.
Active Publication Date: 2021-07-09
CHENGDU UNIVERSITY OF TECHNOLOGY
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[0006] As far as we know, there is no similar literature report with this application
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Embodiment 1
[0012] Add benzaldehyde (1.5 mmol), sodium phenylsulfinate (1.0 mmol), 1,3,5-trimethoxybenzene (1.0 mmol), Amberlyst -15 (50% relative to the mass of 1,3,5-trimethoxybenzene), water (1 ml), and finally seal the ground test tube with a rubber stopper. The test tube was placed in an oil bath at 60°C and stirred for 6 hours. Water (10 mL) was then added to the reaction mixture, and the ion exchange resin was filtered and washed 3 times with ethyl acetate (5 mL). The filtrate was extracted 3 times with ethyl acetate (10 mL), and the combined organic layers were washed with anhydrous MgSO 4 Dry, then adsorb onto some silica gel under reduced pressure on a rotary evaporator. Transfer the silica gel with adsorbed sample to a silica gel column. After purification by silica gel column chromatography (petroleumether: ethyl acetate = 5:1 as eluent), 1,3,5-trimethoxy-2-(phenyl(phenylsulfonyl)methyl) was obtained as a white solid ) Benzene yield is 88%. The reaction equation is shown...
Embodiment 2
[0020] 4-Fluorobenzaldehyde replaces benzaldehyde in Example 1 to obtain the yield of white solid 2-((4-fluorophenyl)(phenylsulfonyl)methyl)-1,3,5-trimethoxybenzene 90%.
[0021] 1 H NMR (400MHz, DMSO-d 6 ):δ7.70–7.60(m,1H),7.59–7.45(m,6H),7.20–7.08(m,2H),6.18(s,2H),6.09(s,1H),3.76(s,3H ),3.62(s,6H);
[0026] 4-Chlorobenzaldehyde replaces benzaldehyde in Example 1 to obtain the yield of white solid 2-((4-chlorophenyl)(phenylsulfonyl)methyl)-1,3,5-trimethoxybenzene 91%.
[0027] 1 H NMR (400MHz, CDCl3 ):δ=7.71-7.62(m,2H),7.59-7.49(m,3H),7.46-7.22(m,4H),6.14(s,1H),6.05(s,2H),3.80(s,3H ),3.64(s,6H).
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Abstract
Sulfones are important pharmaceutical and bioactive compounds. The now popular herbicide mesotrione and bioactive compounds such as gamma-secretase inhibitors belong to the group of sulfones. In addition, sulfone drugs can prevent Alzheimer's disease. Sulfone compounds are also widely used as intermediates in organic synthesis. Among the sulfone compounds, arylmethylalkyl sulfone is an important starting material for the synthesis of triaryl methane, as a leuco dye, a photochromic agent, a structural unit for forming dendrimers, and a substrate for theoretical and biological research. , it has received extensive attention. This patent develops a three-component reaction catalyzed by a recyclable ion exchange resin catalyst Amberlyst‑15 to synthesize arylmethylalkyl sulfones in a wide range of substrates with good yield and excellent yield. One-pot synthesis of arylmethylhydrocarbylsulfones from readily available aryl / alkylaldehydes, sodiumaryl / alkylsulfinates, and polymethoxybenzenes, prepared via C‑C and C‑S bond formation Arylmethylsulfone. The synthesis process has the advantages of particularly mild reaction conditions, simple operation, generally high yield, wide range of substrates, and the like.
Description
technical field [0001] The patent involves the research fields of organic synthesis, drug synthesis, and organic chemical industry. The specific method is to conduct a three-component reaction of sodium hydrocarbyl sulfinate, aryl / alkylaldehyde, and polymethoxybenzene to synthesize arylmethyl hydrocarbyl sulfones in one step. compound. Background technique [0002] Sulfones are important pharmaceutical and bioactive compounds. The now popular herbicide mesotrione and bioactive compounds such as gamma-secretase inhibitors belong to the group of sulfones (D. Cornes, Patent: WO 2002 / 100173. R.A. Wichert and T.H. Beckett, WO 2002 / 019823.). In addition, sulfone drugs can prevent Alzheimer's disease (I.Churcher, D.Beher, J.D.Best, J.L.Castro, E.E.Clarke, A.Gentry, T.Harrison, L.Hitzel, E.Kay, S. Kerrad, H.D. Lewis, P.M. Gutierrez, R.M. Smith, P.J. Oakley, M. Reilly, D.E. Shaw, M.S. Shearman, M.R. Teall, S. Williams and J.D.J. Wrigley, Bioorg. Med. Chem. Lett., 2006, 16, 280.)...
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