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Preparation method of allyl esters

A technology of allyl esters and olefins, applied in the field of organic synthesis, can solve the problems of limited large-scale application, troublesome preparation of reactants, narrow use range of substrates, etc., to achieve improved utilization efficiency, wide range of use, and excellent yield Effect

Inactive Publication Date: 2012-07-25
SUZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although there are many methods for synthesizing allyl esters, many of these methods use transition metals, and some catalysts (such as Ru, Rh, Pd, Ir) are relatively expensive, while some catalytic systems are cumbersome, and some reactants are troublesome to prepare. , the price is more expensive, and the use range of the substrate is narrow, which has great limitations, which limits its large-scale application

Method used

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  • Preparation method of allyl esters
  • Preparation method of allyl esters
  • Preparation method of allyl esters

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024]

[0025] Fill the reaction bottle with Bu 4 NI (20mol%), compound 1a (2mmol, 313.2mg), tert-butyl hydroperoxide (TBHP) (0.4mL), cyclohexene (0.8mL), benzene 8mL; After heating for about 8 hours, it was quenched with saturated sodium sulfite, extracted with ethyl acetate (40 mL×3), dried over anhydrous sodium sulfate, and the oxidation product 3a was obtained by simple column chromatography with a yield of 88%. 1 H NMR (400MHz, CDCl 3 )δ7.98(d, J=8.5Hz, 2H), 7.40(d, J=8.5Hz, 2H), 6.03-5.99(m, 1H), 5.84-5.80(m, 1H), 5.50-5.49(m , 1H), 2.17-1.93(m, 3H), 1.89-1.78(m, 2H), 1.75-1.67(m, 1H); 13 C NMR (100MHz, CDCl 3 )δ165.2, 139.0, 132.9, 130.9, 129.1, 128.5, 125.4, 68.8, 28.3, 24.8, 18.8.MS: Anal.Calcd.For C 13 h 13 35 ClO 2 :236,C 13 h 13 37 ClO 2 : 238, Found: 236 ( 35 Cl), 238( 37 Cl).IR(KBr, cm -1 ): v 1716.

Embodiment 2

[0027]

[0028] Fill the reaction bottle with Bu 4 NI (20 mol%), compound 1a (2 mmol, 313.2 mg), TBHP (0.4 mL), cyclohexene (0.8 mL), cyclohexane 8 mL. Then the system was heated in the air at 80°C for about 8 hours, quenched with saturated sodium sulfite, extracted with ethyl acetate (40mL×3), dried over anhydrous sodium sulfate, and the oxidation product 3a was obtained by simple column chromatography , the yield was 68%. 1 H NMR (400MHz, CDCl 3 )δ7.98(d, J=8.5Hz, 2H), 7.40(d, J=8.5Hz, 2H), 6.03-5.99(m, 1H), 5.84-5.80(m, 1H), 5.50-5.49(m , 1H), 2.17-1.93(m, 3H), 1.89-1.78(m, 2H), 1.75-1.67(m, 1H); 13 C NMR (100MHz, CDCl 3 )δ165.2, 139.0, 132.9, 130.9, 129.1, 128.5, 125.4, 68.8, 28.3, 24.8, 18.8.MS: Anal.Calcd.For C 13 h 13 35 ClO 2 :236,C 13 h 13 37ClO 2 : 238, Found: 236 ( 35 Cl), 238( 37 Cl).IR(KBr, cm -1 ): v 1716.

Embodiment 3

[0030]

[0031] Fill the reaction bottle with Bu 4 NI (20mol%), compound 1a (2mmol, 313.2mg), TBHP (0.4mL), cyclohexene (0.8mL), acetocyanide 8mL. Then the system was heated in the air at 80°C for about 8 hours, quenched with saturated sodium sulfite, extracted with ethyl acetate (40mL×3), dried over anhydrous sodium sulfate, and the oxidation product 3a was obtained by simple column chromatography , the yield was 50%. 1 HNMR (400MHz, CDCl 3 )δ7.98(d, J=8.5Hz, 2H), 7.40(d, J=8.5Hz, 2H), 6.03-5.99(m, 1H), 5.84-5.80(m, 1H), 5.50-5.49(m , 1H), 2.17-1.93(m, 3H), 1.89-1.78(m, 2H), 1.75-1.67(m, 1H); 13 C NMR (100MHz, CDCl 3 )δ165.2, 139.0, 132.9, 130.9, 129.1, 128.5, 125.4, 68.8, 28.3, 24.8, 18.8.MS: Anal.Calcd.For C 13 h 13 35 ClO 2 :236,C 13 h 13 37 ClO 2 : 238, Found: 236 ( 35 Cl), 238( 37 Cl).IR(KBr, cm -1 ): v 1716.

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Abstract

The invention discloses a preparation method of allyl esters, which comprises the following steps: using acid derivative and olefin as reaction substrates; using iodide as a catalyst, using tert-butyl hydroperoxide as an oxidizing agent; reacting through biradical cross coupling reaction to obtain allyl esters. The iodide selects from cuprous iodide, tetramethyl-ammonium iodide, tetraethylammonium iodide, tetrabutyl ammonium iodide or tetraheptylammonium iodide. The invention discloses a new preparation method of allyl esters, the allyl esters can be manufactured directly by means of biradical cross-coupling, therefore, the process step is simple and reliable, the yield ratio is higher, and the better effect is achieved.

Description

technical field [0001] The invention relates to a preparation method of allyl ester, which belongs to the field of organic synthesis. Background technique [0002] Allyl esters are a very important class of compounds that widely exist in natural products and drug molecules with physiological activity, and are often seen in synthetic intermediates. [0003] At present, the method for preparing allyl ester mainly contains: people such as Junzo Otera reported that allyl alcohol and acid prepare allyl ester under the effect of organic fluorine reagent (referring to Angew.Chem.Int.Ed.2002,41,4117- 4119); B.M.Choudary et al. reported that allyl alcohol and acid prepared allyl esters under the action of natural kaolinite (see Green Chem., 2000, 2, 67-70); S.J.Kulkarni et al. reported microwave action Allyl alcohol and acid involved in zeolite prepare allyl ester (see Green Chem., 2006, 8, 368-372); Brindaban C.Ranu et al. reported that allyl alcohol and acid halide prepare allyl e...

Claims

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Application Information

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IPC IPC(8): C07C67/04C07C69/773C07C69/767C07C69/76C07C69/73C07C69/74C07C69/65C07C69/92C07C205/57C07C201/12C07C229/10C07C227/16C07C255/50C07C317/44C07D209/48C07D231/56C07D307/68C07D307/85
Inventor 万小兵时二波陈书林刘召军张杰
Owner SUZHOU UNIV
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