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A kind of method that carboxylic acid is reduced into aldehyde compound
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A technology of aldehyde compounds and compounds, applied in the preparation of organic compounds, organic chemical methods, chemical instruments and methods, etc., can solve problems such as unfavorable promotion, limited scope of substrate applicability, and ineffective reduction of aromatic carboxylic acids, etc. Achieve the effects of simple and easy operation, wide substrate universality and improved efficiency
Active Publication Date: 2022-05-17
ZHENGZHOU UNIV
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[0004] Although these synthetic methods are mature, the scope of applicability of substrates is still very limited. For example, bromo- and iodo-aromatic carboxylic acids cannot be effectively reduced. In addition, the use of noble metalpalladium as a catalyst is not conducive to popularization.
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[0026] In a dry 10mL Schlenk reaction tube, add n-decanoic acid (86mg, 0.50mmol), then add L1 (3.9mg, 0.025mmol), NiCl 2 DME (1.1mg, 0.005mmol), under the protection of argon, add toluene (1.0mL), pivalic anhydride (120μL, 0.60mmol), H 2 SiEt 2 (19μL, 0.15mmol), react at 45°C for 5h. After the reaction, extract, remove the solvent under reduced pressure, and separate by column chromatography (petroleumether / ethyl acetate=13 / 1, volume ratio) to obtain the target product A. Experimental data of this compound: Colorlessliquid, isolated yield 75%, mp: 8°C; 1H NMR (400MHz, CDCl 3 ):δ=9.8(t,1H),2.1-2.6(m,2H),1.1-1.6(m,14H),1.0(t,3H); 13 C NMR (CDCl 3 ,200MHz): δ=201.2, 41.9, 30.5, 29.7, 29.1, 29.0, 28.9, 21.5, 21.0, 14.1.
Embodiment 2
[0028] Preparation of Compound B:
[0029]
[0030] Add 4-tert-butylcyclohexylcarboxylic acid (64mg, 0.50mmol) to a dry 10mL Schlenk reaction tube, then add L2 (11mg, 0.050mmol), NiCl 2 (dppe) (9.6mg, 0.025mmol), under the protection of argon, add THF (1.0mL), acetic anhydride (95μL, 1mmol), H 2 SiMePh (76 μL, 0.55 mmol), react at 60° C. for 8 h. After the reaction, extract, remove the solvent under reduced pressure, and separate by column chromatography (petroleumether / ethyl acetate=13 / 1, volume ratio) to obtain the target product B. The experimental data of the compound The experimental data of the compound: Yellow liquid, isolated yield 75%, mp: N / A; 1 HNMR (400MHz, CDCl 3 ):δ=9.73(d,J=1.80Hz,1H),2.25-2.16(m,1H),2.15-2.07(m,2H),1.81-1.71(m,2H),1.02-1.252(m,2H ),0.98-1.83(m,3H,),0.76(s,9H).
[0034] Add 3-iodobenzoic acid (124mg, 0.50mmol) to a dry 10mL Schlenk reaction tube, then add L3 (9mg, 0.050mmol), NiCl 2 (dppe) (9.6mg, 0.025mmol), under the protection of argon, add THF (1.0mL), acetic anhydride (95μL, 1mmol), H 2 SiMePh (76 μL, 0.55 mmol), react at 60° C. for 8 h. After the reaction, extract, remove the solvent under reduced pressure, and separate by column chromatography (petroleumether / ethyl acetate=13 / 1, volume ratio) to obtain the target product C. The experimental data of the compound The experimental data of the compound: White solid, isolated yield 78%, mp: 59-62°C; 1 H NMR (400MHz, CDCl 3 ):δ=7.30(t,J=7.31Hz,1H),7.88(m,1H),7.99(m,1H),8.24(t,J=1.7Hz,1H),9.96(s,1H). 13 C NMR (200MHz, CDCl 3 ): δ=93.60, 126.8, 131.7, 138.3, 138.7, 144.1, 192.4.
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Abstract
The invention discloses a method for reducing carboxylic acid into aldehyde compounds, belonging to the field of organic chemical synthesis. Specifically, under an argonatmosphere, dissolve carboxylic acid compounds, transition metalnickel compounds, acid anhydride compounds, ligands, and reducing agents in an organic solvent, heat and stir the reaction, and remove the organic solvent under reduced pressure after the reaction is complete. Column chromatographic separation was carried out to obtain various aldehyde compounds. The invention has simple synthesis steps, mild reaction conditions, and simple and easy operation, can successfully reduce carboxylic acid compounds to aldehyde organic compounds, and has a small amount of reaction catalyst and high product yield, providing a source for the reduction of carboxylic acid compounds to aldehyde compounds. a new way. Compared with existing methods, the raw materials are cheap, easy to obtain and environmentally friendly, which increases the universality of substrates and the compatibility of functional groups, and has certain innovation and unique research significance in organic synthesis methodology.
Description
technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for reducing carboxylic acids to aliphatic aldehydes or aromatic aldehydes. Background technique [0002] Aldehydes are widely used intermediates in the process of synthesizing many organic compounds, and the synthesis of aldehydes from carboxylic acid derivatives is an important transformation method commonly used in industrial and laboratory organic synthesis. The traditional transformation method is generally It consists of two steps: first, the reduction of carboxylic acid to alcohol, and then the oxidation of alcohol to the corresponding aldehyde. [R.C.Larock, Comprehensive Organic Transform-ation: A Guide to Functional Group Preparation, 2nd ed., Wiley-VCH, New York, 1999, 46(2), 195-196.] Among them, the reduction of carboxylic acid derivatives into alcohols is usually Metalhydride reagents are required, such as lithiumaluminum hydride, sodium borohy...
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