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Method for preparing 4-ethynyl-2,4-dimethyl-1,3-dioxane

A technology of dioxane and dimethyl, which is applied in the field of synthesis of 4-ethynyl-2,4 dimethyl-1,3-dioxane, can solve problems such as not being a better method, and achieve raw materials Reagents are cheap, industrialized, and easy to industrialize

Inactive Publication Date: 2014-11-26
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0017] In summary, the current methods for preparing 4-ethynyl-2,4-disubstituted-1,3-dioxane compounds are not optimal methods

Method used

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  • Method for preparing 4-ethynyl-2,4-dimethyl-1,3-dioxane

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: the preparation of intermediate one ：

[0029] Add 625 mL (1.0 mol) of 1.6 mol / L THF solution of ethynylmagnesium bromide in a 1 L three-necked flask, and drop 80.09 g (0.5 mol) of 4-(1-ethoxyethoxy base)-2-butanone; after dropping, TLC (petroleum ether: ethyl acetate=3:1, R f = 0.3) to detect the end of the reaction, and the reaction was completed in about 0.5 hours. Add 500 mL of saturated NH with stirring 4 Cl solution was hydrolyzed, the organic layer was separated, the aqueous layer was extracted three times with 100 mL of ethyl acetate, the combined organic layers were washed once with 80 mL of saturated brine, and anhydrous Na 2 SO 4 dry. Then the solvent was evaporated, and Intermediate 1 was obtained by separation and purification with a yield of 65%.

[0030] The infrared that intermediate one test obtains, nuclear magnetic resonance and mass spectrum data are as follows: FT-IR (film) (cm -1 ): 3443, 3295, 2979, 2929, 2884, 2106, 1716...

Embodiment 2

[0031] Embodiment 2: the preparation of target object:

[0032] Add 18.60 g (0.1 mol) of Intermediate 1 and 50 mL of anhydrous EtOH into a 100 mL three-necked flask, then pass through dry HCl (g) at 10-15°C, TLC (petroleum ether: ethyl acetate=8: 1, R f = 0.5) to detect the end point of the reaction, the reaction is completed in about 1 hour, and the reaction solution is filled with saturated NaHCO 3 Wash to neutral, anhydrous Na 2 SO 4 dry. The solvent was evaporated, and the target product was obtained by distillation under reduced pressure with a yield of 60%.

[0033] The infrared, nuclear magnetic resonance and mass spectrometry data obtained by the target test are as follows: FT-IR (film) (cm -1 ): 3293, 2988, 2929, 2867, 2106, 1728, 1402, 1260, 1192, 1136, 1095, 944, 858; 1 H NMR (400 MHz, CDCl 3 ): δ (ppm) = 5.16 (q, J = 5.2 Hz, 1H, CHCH 3 ), 4.08-3.94 (m, 2H, CH2 O), 2.54 (s, 1H, ethynyl), 1.89 (td, J = 12.8, 4.8 Hz, 1H), 1.59 (td, J = 13.2, 1.6 Hz...

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Abstract

The invention relates to a method for preparing 4-ethynyl-2,4-dimethyl-1,3-dioxane, wherein 4-(1-ethoxyethoxy)-2-butanone is adopted as a raw material, and a two-step reaction is performed to synthesize the 4-ethynyl-2,4-dimethyl-1,3-dioxane. Compared with methods for preparing the 4-ethynyl-2,4 disubstituted-1,3-dioxane compound in the prior art, the method of the present invention has advantages of cheap raw material reagent, short synthesis step, mild reaction condition, easy industrialization and the like.

Description

Technical field [0001] The invention involves the field of organic synthesis, which is a new method of synthetic synthesis of 4-acetylene-2,4-1,3-six-base-1,3-six-year-in-law. Background technique [0002] 4-acetylene-2,4 replacement -1,3-epoxy sixth ring type compound (structural form 1) is an important intermediate that can be used to synthesize Aflastatin A [Organic Letters, 2008, 10(9): 1811-1814.], Peinan antibiotics carbapenams [The Journal of Organic Chemistry, 2010, 75 (22): 7580-7587.] And vitamin A [de1056621], etc.Aflastatin A can inhibit the biological synthesis of yellow mold without allowing parasitic mold to grow. In addition, Aflastatin A also has antibacterial activity and antitumor activity; Class Classic antibiotic Carbapenams is a new type of β-laidide antibiotic.It is used in the treatment of severe infections caused by unknown disease; and vitamin A can maintain the normal visual function of the human body, promote the normal growth and development of bones,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D319/06
CPCC07D319/06
Inventor 王玉良蒲帅吴凯群
Owner SICHUAN UNIV