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Chloromethyl methyl ether and synthesis method of compound protected by methoxymethyl thereof

A technology of chloromethyl methyl ether and synthesis method, applied in the direction of preparation of organic compounds, steroids, chemical instruments and methods, etc., can solve the problem of easy hydrolysis deactivation, blockage of reactor pipes, and unsuitability for continuous flow reactors and other issues, to achieve the effect of fast response speed

Inactive Publication Date: 2015-06-17
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, ZnBr 2 Very easy to deactivate by hydrolysis, if the raw materials used in the reaction are not dried or the water vapor cannot be strictly isolated during the reaction, the reaction may be terminated
At the same time due to ZnBr 2 Presence of solids, which may clog reactor tubes, making it unsuitable for continuous flow reactors

Method used

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  • Chloromethyl methyl ether and synthesis method of compound protected by methoxymethyl thereof
  • Chloromethyl methyl ether and synthesis method of compound protected by methoxymethyl thereof
  • Chloromethyl methyl ether and synthesis method of compound protected by methoxymethyl thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The synthesis of embodiment 1 chloromethyl methyl ether (MOMCl) (IV)

[0026]

[0027] Dissolve 26mL (0.225 mol) of benzoyl chloride (I) and 20mL (0.225 mol) of dimethoxymethane (II) in a 100mL reaction flask, add 0.6mL (3 mol%) of trifluoromethanesulfonic acid, and next reaction, 1 H NMR monitoring, 0.5h reaction complete. Post-processing: the resulting reaction solution was pumped into a cleaned cold trap under a water bath, and then distilled at 80°C under normal pressure to obtain 17.85 g of pure product MOMCl(IV), with an isolation yield of 98%.

[0028] Compound (IV): molecular weight, 80.51; 1 H NMR (400MHz, CDCl 3 ):δ5.45(s,2H),3.50(s,3H).

[0029](NMR references: Reggelin, M.; Doerr, S.A Modified Low-cost Preparation of Chloromethyl Methyl Ether (MOM-Cl). Synlett. 2004, 6, 1117-1117.)

Embodiment 2

[0030] Embodiment 2 The synthesis of chloromethyl methyl ether (MOMCl) (IV)

[0031]

[0032] Dissolve 16mL (0.225 mol) of acetyl chloride (V) and 20mL (0.225 mol) of dimethoxymethane (II) in a 100mL reaction flask, and slowly add 0.6mL (3 mol%) of trifluoromethanesulfonate at 0°C acid, and then raised to room temperature at 20°C to react, 1 H NMR monitoring, the reaction is complete in less than 10 minutes.

[0033] Compound (IV): molecular weight, 80.51; 1 H NMR (400MHz, CDCl 3 ):δ5.45(s,2H),3.50(s,3H).

[0034] Compound (VI): molecular weight, 74.08; 1 H NMR (400MHz, CDCl 3 ): δ3.66(s,3H),2.05(s,3H).

Embodiment 3

[0035] Example 3 Synthesis of 19-methoxymethoxyandrost-4-ene-3,17-dione (VIII)

[0036]

[0037] Dissolve 5.2 mL (0.045 mol) of benzoyl chloride and 4 mL (0.045 mol) of dimethoxymethane in a 25 mL reaction flask, add 0.12 mL (3 mol %) of trifluoromethanesulfonic acid, and react at 60°C for 0.5 h, After cooling to room temperature, directly and slowly add 6.80g (0.0225 moles) of 19-hydroxyandrost-4-ene-3,17-dione (VII) and 14.9mL (0.09 moles) of N,N-diisopropyl 22.5 mL of dichloromethane solution of ethyl ethylamine to react for 0.5 hour, or monitor the reaction by thin layer chromatography (TLC) until complete. Post-treatment: Pour the reaction system into 30 mL of saturated sodium bicarbonate solution, add 10 mL of dichloromethane, stir thoroughly for 10 minutes, separate the liquids, extract the aqueous phase twice with 15 mL of dichloromethane each time, combine the organic phases, and then wash with water , washed with saturated brine, dried over anhydrous sodium sulfa...

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Abstract

The invention provides chloromethyl methyl ether and a synthesis method of a compound protected by methoxymethyl thereof. The chloromethyl methyl ether (MOMCl) is a common protective reagent in organic synthesis. Commonly used synthesis methods are tedious in operation and long in reaction time. The synthesis method provided by the invention comprises: with trifluoromethane sulfonic acid or perchloric acid as a catalyst, reacting acyl chloride with dimethoxymethane to synthesize the chloromethyl methyl ether. The chloromethyl methyl ether produced in situ can directly act with a hydroxyl compound and organic alkali dissolved in an organic solvent to generate a product with hydroxyl protected by MOM. The method has the advantages of high reaction speed and simple reaction operation. Therefore, the method can be applicable to the production and application of a continuous flow reactor.

Description

technical field [0001] The invention relates to a method for rapidly synthesizing chloromethyl methyl ether (MOMCl) and its methoxymethyl-protected compound. Using this method to generate MOMCl in situ in a continuous flow reactor, it can directly react with hydroxyl compounds under alkaline conditions to generate protected hydroxyl compounds. Background technique [0002] Chloromethyl methyl ether (MOMCl) is a more important hydroxyl protection reagent in organic synthesis, it can convert hydroxyl compounds into methoxymethyl (MOM) ether compounds. Commercially available MOMCl contains bis(chloromethyl)ether, which is highly carcinogenic, and methods have been developed that do not produce toxic by-products. Meanwhile, low-boiling MOMCl is listed as an extremely toxic substance by the EPA and the European Union, so its use and disposal are restricted by regulations. In China, since 2002, MOMCl has been prohibited from being traded as a commercial reagent. Synthesis must ...

Claims

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Application Information

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IPC IPC(8): C07C43/17C07C41/22C07J7/00C07J1/00C07J75/00C07C43/164C07C41/16
Inventor 丁凯曹伟
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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