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A kind of synthetic method of 3-aminomethyltetrahydrofuran

A technology of aminomethyltetrahydrofuran and its synthesis method, which is applied in the direction of organic chemistry, can solve the problems of expensive raw materials, difficult process conditions, and many times of noble metal catalysis, and achieve the effects of easy-to-obtain raw materials, simple operation, and reasonable design

Active Publication Date: 2020-03-17
DALIAN JOIN KING FINE CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The above process route has the disadvantages of using precious metals for many times of catalysis, using highly toxic cyanide, using strong alkali with potential safety hazards, high raw material costs, or difficult process conditions.

Method used

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  • A kind of synthetic method of 3-aminomethyltetrahydrofuran
  • A kind of synthetic method of 3-aminomethyltetrahydrofuran
  • A kind of synthetic method of 3-aminomethyltetrahydrofuran

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Step 1: Add furan (68.0g, 1.0mol) and 340.0g N,N-dimethylformamide to a 1L reaction flask, cool down to 0°C, add liquid bromine (159.8g, 1.0mol) dropwise, and control the temperature Do not exceed 25 ° C, after 1 hour of dripping, continue to keep stirring for 1 hour.

[0023] Add 100 g of water, then extract with 100 g of petroleum ether (60-90 boiling range) x 3, combine the obtained petroleum ether layers, and add 100 g of water to wash. The petroleum ether solution of 2-bromofuran obtained after washing was directly used in the next step without further treatment.

[0024] In the 2nd step, add paraformaldehyde (60.0g, 2.0mol), concentrated hydrochloric acid (202.5g, 2.0mol, 36Wt%), polyethylene glycol 400 (20.0g) in 2L reaction bottle, heat up to 50 ℃, drop Add a petroleum ether solution of 2-bromofuran (1.0 mol, the number of moles of the raw material used in the first step is still used), drop it for 1.0 h, and then continue to keep stirring for 2.0 h.

[0025] ...

Embodiment 2

[0034] step 1:

[0035] With reference to the operation of the first step of Example 1, the reaction conditions were changed to obtain the results in Table 1.

[0036] Table 1

[0037]

[0038]

[0039] Step 2:

[0040] With reference to the operation of the second step of Example 1, the reaction conditions were changed to obtain the results in Table 2.

[0041] Table 2

[0042] experiment number Paraformaldehyde hydrochloric acid phase transfer catalyst temperature yield 1 1.0eq 1.0eq Polyethylene glycol 400, 0.05eq 50℃ 51％ 2 1.5eq 1.5eq Polyethylene glycol 400, 0.05eq 50℃ 70％ 3 3.0eq 3.0eq Polyethylene glycol 400, 0.05eq 50℃ 84％ 4 2.0eq 2.0eq Polyethylene glycol 400, 0.02eq 50℃ 74％ 5 2.0eq 2.0eq Polyethylene glycol 400, 0.1eq 50℃ 85％ 6 2.0eq 2.0eq Tetrabutylammonium chloride, 0.05eq 50℃ 75％ 7 2.0eq 2.0eq Polyethylene glycol 400, 0.05eq 40℃ 77％ 8 2.0eq 2.0eq ...

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Abstract

The invention discloses a synthetic method of 3-aminomethyl tetrahydrofuran and belongs to the technical field of organic chemistry. The synthetic method takes furan as a raw material and sequentiallycomprises the following steps: 1, bromination; 2, chloromethylation; 3, ammoniation; 4, deprotection; and 5, reduction so as to obtain the 3-aminomethyl tetrahydrofuran. The method has the advantagesthat the raw materials are easy to obtain, the reaction conditions of all steps are simple, virulent reagents or reagents with great potential safety hazards are not used, and a synthetic route for pesticide intermediates is enriched.

Description

Technical field: [0001] The invention belongs to the field of organic chemistry, and in particular relates to a synthesis method of 3-aminomethyltetrahydrofuran. Background technique: [0002] 3-aminomethyltetrahydrofuran is an important intermediate for the synthesis of the nicotinic insecticide dinotefuran, and the methods for the synthesis of 3-aminomethyltetrahydrofuran that have been reported in the existing literature mainly contain the following: [0003] 1) Using 1,4-butenediol as a raw material, undergo cyclization, hydroformylation, amination, and hydrogenation reduction to prepare 3-aminomethyltetrahydrofuran (see: CN106397372, CN106866588). [0004] 2) Using γ-butyrolactone as a raw material, undergo hydroxymethylation, reduction, esterification, ammoniation, hydrazinolysis (refer to: CN106349196), or undergo halogenation, reduction, dehydration and cyclization, cyanide cyanide, addition Hydrogen reduction (see: CN106749116) to prepare 3-aminomethyltetrahydrofur...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/14
CPCC07D307/14
Inventor 戴耀王海英王荣良王延波
Owner DALIAN JOIN KING FINE CHEM CO LTD