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(2-alkoxy-4-oxo)-penta-2-enoate compound preparation method

An alkoxy and alkenoate technology, which is applied in the field of preparation of -pent-2-enoate compounds, can solve the problems of equipment corrosion, waste acid water generation, complicated post-treatment, etc., and achieves mild reaction conditions and environmental protection. The effect of less pollution and easy operation

Inactive Publication Date: 2007-07-11
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Claiser et al. reported (Chem Ber, 1907, 40, 3903) to prepare (2-ethoxy-4- Oxo)-pent-2-enoic acid ethyl ester (I), but the reaction time of this method can be completed for up to 7 days and the aftertreatment is loaded down with trivial details
Chinese patent announcement number is 1216992 Chinese patent has described the method that acetylacetonate and orthoformate condensation reaction prepares class I compound with methanesulfonic acid or concentrated sulfuric acid etc. as catalyst, although the reaction time of this method is greatly shortened, but There is a large amount of waste acid water, serious environmental pollution or strong corrosion of equipment

Method used

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Embodiment 1

[0020] Embodiment 1: Preparation of (2-methoxy-4-oxo)-pent-2-enoic acid methyl ester (I)

[0021] Methyl acetylacetonate (14.4 g, 0.1 mol), trimethyl orthoformate (11.7 g, 0.11 mol), polystyrene-supported ferric chloride (6.8 g, 0.01 mol) and anhydrous methanol (25 mL) were placed Dry the reaction bottle and stir it well at 45°C for 5h. After the reaction is complete, cool to room temperature, filter, recover the catalyst, and recover methanol from the filtrate under reduced pressure. Add ethyl acetate (150mL) to the residue, continue to stir for 5min, let it stand, separate the organic layer, and wash with 10% sodium carbonate solution (20mL×5), water (20mL×3), saturated saline (20mL×3) successively 2) Wash and dry over anhydrous magnesium sulfate. After recovering the solvent, distill under reduced pressure and collect fractions at 107-109°C / 13mmHg to obtain light yellow oil I (R 1 =R 2 =CH 3 , 13.4g, 85%). The purity is 98.2% (GC-MS).

[0022] 1 H NMR (CDCl 3 ): δ=...

Embodiment 2

[0024] Embodiment 2: Preparation of (2-methoxy-4-oxo)-pent-2-enoic acid methyl ester (I)

[0025] Methyl acetylacetonate (14.4 g, 0.1 mol), trimethyl orthoformate (31.9 g, 0.3 mol), polystyrene-supported titanium tetrachloride (139.8 g, 0.2 mol) and anhydrous methanol (50 mL) were placed Dry the reaction bottle and stir it well at 60°C for 2h. After the reaction is complete, cool to room temperature, filter, recover the catalyst, and recover methanol from the filtrate under reduced pressure. Add ethyl acetate (200mL) to the residue, continue stirring for 5min, let it stand, separate the organic layer, and wash with 10% sodium carbonate solution (30mL×5), water (30mL×3), saturated saline (30mL×3) successively 2) Wash and dry over anhydrous magnesium sulfate. After recovering the solvent, distill under reduced pressure, collect 107-109 ℃ / 13mmHg fraction, obtain light yellow oily product I (R 1 =R 2 =CH 3 , 14.2g, 90%). The purity is 98% (GC-MS). 1 Both HNMR and MS are con...

Embodiment 3

[0026] Embodiment 3: Preparation of (2-ethoxyl-4-oxo)-pent-2-enoic acid ethyl ester (I)

[0027] Ethyl acetylacetonate (15.8 g, 0.1 mol), triethyl orthoformate (16.3 g, 0.11 mol), polystyrene-loaded ferric chloride (6.8 g, 0.01 mol) and absolute ethanol (25 mL) were placed Dry the reaction bottle and stir it well at 45°C for 5h. After the reaction is complete, cool to room temperature, filter, recover the catalyst, and recover methanol from the filtrate under reduced pressure. Add ethyl acetate (150mL) to the residue, continue to stir for 5min, let it stand, separate the organic layer, and wash with 10% sodium carbonate solution (20mL×5), water (20mL×3), saturated saline (20mL×3) successively 2) Wash and dry over anhydrous magnesium sulfate. After recovering the solvent, distill under reduced pressure, collect 127-129 ° C / 11mmHg fractions, and obtain light yellow oily substance I (R 1 =R 2 =C 2 h 5 , 16.7g, 90%). The purity is 98.2%. (GC-MS).

[0028] 1 H NMR (CDCl...

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PUM

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Abstract

The invention discloses a making method of 2-alkoxy-4-oxo-peta-2-alkylene acid ester compound in the organic chemical technical domain, which is characterized by the following: shortening reacting time; improving receiving rate; avoiding three-slag pollution; condensing acetylacetonate and orthoformate in the aliphatic alcohol catalyzed by acid to obtain the product.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and in particular relates to a preparation method of (2-alkoxy-4-oxo)-pent-2-enoate compounds (I). [0002] [0003] where R 1 =R 2 =C 1 -C 4 alkyl. Background technique [0004] (2-Alkoxy-4-oxo)-pent-2-enoate compounds (I) are synthetic 20(S)-camptothecins [20(S)-Camptothecins] antitumor drugs such as camptothecin Basic compounds (Camptothecin), hydroxycamptothecin (20(S)-10-Hydroxycamptothecin), topotecan (Topotecan), irinotecan (Irinotecan), etc., and important intermediates of natural medicines with biological activity. [0005] Claiser et al. reported (Chem Ber, 1907, 40, 3903) to prepare (2-ethoxy-4- Oxo)-pent-2-enoic acid ethyl ester (I), but the reaction time of this method is as long as 7 days before it can be completed and the aftertreatment is loaded down with trivial details. Chinese patent announcement number is 1216992 Chinese patent has described the method that...

Claims

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Application Information

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IPC IPC(8): C07C67/31C07C69/716B01J31/08
Inventor 陈芬儿赵磊
Owner FUDAN UNIV
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