AU2018100831A4 - Organic synthesis intermediates 2-tetrolaldehyde synthesis method - Google Patents
Organic synthesis intermediates 2-tetrolaldehyde synthesis method Download PDFInfo
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- AU2018100831A4 AU2018100831A4 AU2018100831A AU2018100831A AU2018100831A4 AU 2018100831 A4 AU2018100831 A4 AU 2018100831A4 AU 2018100831 A AU2018100831 A AU 2018100831A AU 2018100831 A AU2018100831 A AU 2018100831A AU 2018100831 A4 AU2018100831 A4 AU 2018100831A4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
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Abstract
Organic synthesis intermediates 2-tetrolaldehyde synthesis method Abstract 5 The present invention discloses organic synthesis intermediates 2-tetrolaldehyde synthesis method, comprises the following steps: 1-bromo-2-butyne and anhydrous butyl ether solution were added to the reaction vessel, controlled the stirring speed, controlled the temperature of the solution, added lanthanum oxide powder in batches, reacted; then added anhydrous acetic acid-3-methoxy butyl solution, raised the 10 temperature of the solution, reacted, added anhydrous 2,4-two methyl sulfolane solution, re-fluxed, washed with anhydrous N, N-two acetamide solution for several times, washed with anhydrous two glycol two methyl ether for several times, recrystallized in the anhydrous two hexyl amine solution, dehydrated with dehydration, got the finished product 2-tetrolaldehyde.
Description
The present invention discloses organic synthesis intermediates 2-tetrolaldehyde synthesis method, comprises the following steps: l-bromo-2-butyne and anhydrous butyl ether solution were added to the reaction vessel, controlled the stirring speed, controlled the temperature of the solution, added lanthanum oxide powder in batches, reacted; then added anhydrous acetic acid-3-methoxy butyl solution, raised the temperature of the solution, reacted, added anhydrous 2,4-two methyl sulfolane solution, re-fluxed, washed with anhydrous N, N-two acetamide solution for several times, washed with anhydrous two glycol two methyl ether for several times, recrystallized in the anhydrous two hexyl amine solution, dehydrated with dehydration, got the finished product 2-tetrolaldehyde.
2018100831 19 Jun2018
Organic synthesis intermediates 2-tetrolaldehyde synthesis method
FIELD OF THE INVENTION
The present invention relates to a method for preparing a pharmaceutical 5 intermediate which belongs to the field of organic synthesis, more particularly, relates to organic synthesis intermediates 2-tetrolaldehyde synthesis method.
GENERAL BACKGROUND
2-tetrolaldehyde is mainly used as intermediates of organic synthesis, most of the existing synthesis methods adopt chromic acid, pyridine and chloride mixed solution as one of the reactants, because make the chromic acid as reactant polluting environment, and lead to follow-up pollutant treatment cost high; make chloride as reactant requirement the precursors of equipment corrosion higher, and equipment maintenance and the production cost will be higher, and the synthesis method is complicated. Therefore, it is necessary to propose a new synthesis method.
SUMMARY
Based on the technical problems of the background technology, the purpose of the present invention is to provide organic synthesis intermediates 2-tetrolaldehyde synthesis method, comprises the following steps:
A: l-Bromo-2-butyne and 900ml anhydrous butyl ether solution were added to 20 the reaction vessel, controlled the stirring speed at 130-160 rpm, controlled the temperature of the solution to 10-16 °C, added lanthanum oxide powder in batches, reacted for 90-130 min;
B: then added anhydrous acetic acid-3-methoxy butyl solution, raised the temperature of the solution to 20-25 °C, reacted for 50-80 min, added 1.3L anhydrous
2,4- two methyl sulfolane solution, re-fluxed 2-3h, washed with anhydrous N, N-two acetamide solution for several times, washed with anhydrous two glycol two methyl ether for several times, recrystallized in the anhydrous two hexyl amine solution, dehydrated with dehydration, got the finished product 2-tetrolaldehyde.
Preferably, the dehydration is anhydrous potassium carbonate, any of the
2018100831 19 Jun 2018 anhydrous magnesium sulfate.
Throughout the reaction process can be the following reaction formula: CH3C=C-CH, + LaA + C7H,403 -CHjC=C—
Br
CHj
Compared with the synthetic method disclosed in the background art, the invention provides organic synthesis intermediates 2-tetrolaldchyde synthesis method, it is unnecessary to use elu'omic acid, pyridine and chloride as reactions, avoid the environmental pollution of chromic acid and decrease the follow-up pollutant treatment cost; meanwhile reduce chloride as reactant requirement the precursors of equipment corrosion higher malpractice, and equipment maintenance and the production cost will be lower, at the same time, reducing intermediate links reaction, decreasing the reaction time and improving the reaction yield, the present invention provides a new synthetic route which has laid a good foundation for further enhancing the yield of the reaction.
DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS
The following examples with reference to specific embodiments of the present invent io n are fur thcr i I lust rated:
Embodiment 1
Organic synthesis intermediates 2-tetrolaIdehydc synthesis method, comprises the following steps;
A: 2mol l-Brojno-2-butyne and 900ml anhydrous butyl ether solution were added to the reaction vessel, controlled the stirring speed at l30rpm, controlled the temperature of the solution to IOC , added 2mol lanthanum oxide powder in batches, reacted for 90min;
B: then added 2mol anhydrous acetic acid-3-mcthoxy butyl solution, raised the temperature of the solution to 20C , reacted for 50min, added L3L anhydrous 2,425 two methyl sulfolane solution, re-fluxed 2h, washed with anhydrous N, N-two acetamide solution for two times, washed with anhydrous two glycol two methyl ether for four times, recrystal I tzed in the anhydrous two hexyl amine solution, dehydrated with anhydrous potassium carbonate dehydration, got the finished product
2018100831 19 Jun 2018
2-tetrolaldehyde 116.96g, yield of 86%.
Embodiment 2
Organic synthesis intermediates 2-tetrolaldehyde synthesis method, comprises the following steps:
A: 2mol l-Bromo-2-butyne and 900ml anhydrous butyl ether solution were added to the reaction vessel, controlled the stirring speed at 150rpm, controlled the temperature of the solution to 15 °C , added 2.8mol lanthanum oxide powder in batches, reacted for 120min;
B: then added 3mol anhydrous acetic acid-3-methoxy butyl solution, raised the 10 temperature of the solution to 24°C , reacted for 75min, added 1.3L anhydrous 2,4two methyl sulfolane solution, re-fluxed 2.7h, washed with anhydrous N, N-two acetamide solution for three times, washed with anhydrous two glycol two methyl ether for five times, recrystallized in the anhydrous two hexyl amine solution, dehydrated with anhydrous magnesium sulfate dehydration, got the finished product
2-tetrolaldehyde 123.76g, yield of 91%.
Embodiment 3
Organic synthesis intermediates 2-tetrolaldehyde synthesis method, comprises the following steps:
A: 2mol l-Bromo-2-butyne and 900ml anhydrous butyl ether solution were added 20 to the reaction vessel, controlled the stirring speed at 160rpm, controlled the temperature of the solution to 16 °C, added 3mol lanthanum oxide powder in batches, reacted for 130min;
B: then added 4mol anhydrous acetic acid-3-methoxy butyl solution, raised the temperature of the solution to 25 °C, reacted for 80min, added 1.3L anhydrous 2,4- two methyl sulfolane solution, re-fluxed 3h, washed with anhydrous N, N-two acetamide solution for four times, washed with anhydrous two glycol two methyl ether for six times, recrystallized in the anhydrous two hexyl amine solution, dehydrated with anhydrous potassium carbonate dehydration, got the finished product 2-tetrolaldehyde 127.84g, yield of 94%.
The embodiments of the present invention are merely preferred embodiments of
2018100831 19 Jun2018 the present invention, but the range of the present invention is not limited this, and any person who is familiar with those skilled in the arts, within the technical range of the present invention. It is intended that the technical solution and its inventive concept be replaced or modified equivalently with reference to the range of the invention.
2018100831 19 Jun 2018
Claims (2)
- Claims1. Organic synthesis intermediates 2-tetrolaldehyde synthesis method, comprises the following steps:5 A: l-bromo-2-butyne and 900ml anhydrous butyl ether solution were added to the reaction vessel, controlled the stirring speed at 130-160rpm, controlled the temperature of the solution to 10-16°C, added lanthanum oxide powder in batches, reacted for 90-130 min;B: then added anhydrous acetic acid-3-methoxy butyl solution, raised the 10 temperature of the solution to 20-25°C, reacted for 50-80min, added 1.3L anhydrous 2,4-two methyl sulfolane solution, re-fluxed 2-3h, washed with anhydrous N, N-two acetamide solution for several times, washed with anhydrous two glycol two methyl ether for several times, recrystallized in the anhydrous two hexyl amine solution, dehydrated with dehydration, got the finished product 2-tetrolaldehyde.
- 2. Organic synthesis intermediates 2-tetrolaldehyde synthesis method according to claim 1 wherein the dehydration is anhydrous potassium carbonate, any of the anhydrous magnesium sulfate.20 3. Organic synthesis intermediates 2-tetrolaldehyde synthesis method according to claim 1 wherein, comprises the following steps:A: 2mol l-bromo-2-butyne and 900ml anhydrous butyl ether solution were added to the reaction vessel, controlled the stirring speed at 160rpm, controlled the temperature of the solution to 16 °C, added 3mol lanthanum oxide powder in batches,25 reacted for 130min;B: then added 4mol anhydrous acetic acid-3-methoxy butyl solution, raised the temperature of the solution to 25°C, reacted for 80min, added 1.3L anhydrous 2,4two methyl sulfolane solution, re-fluxed 3h, washed with anhydrous N, N-two2018100831 19 Jun 2018 acetamide solution for four times, washed with anhydrous two glycol two methyl ether for six times, recrystallized in the anhydrous two hexyl amine solution, dehydrated with anhydrous potassium carbonate dehydration, got the finished product 2-tetrolaldehyde.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710531842.3A CN108238866A (en) | 2017-07-03 | 2017-07-03 | The synthetic method of organic synthesis intermediate 2- tetrolaldehydes |
| CN2017105318423 | 2017-07-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2018100831A4 true AU2018100831A4 (en) | 2018-08-09 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2018100831A Ceased AU2018100831A4 (en) | 2017-07-03 | 2018-06-19 | Organic synthesis intermediates 2-tetrolaldehyde synthesis method |
Country Status (3)
| Country | Link |
|---|---|
| CN (1) | CN108238866A (en) |
| AU (1) | AU2018100831A4 (en) |
| GB (1) | GB201713544D0 (en) |
-
2017
- 2017-07-03 CN CN201710531842.3A patent/CN108238866A/en active Pending
- 2017-08-23 GB GBGB1713544.3A patent/GB201713544D0/en not_active Ceased
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2018
- 2018-06-19 AU AU2018100831A patent/AU2018100831A4/en not_active Ceased
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| Publication number | Publication date |
|---|---|
| GB201713544D0 (en) | 2017-10-04 |
| CN108238866A (en) | 2018-07-03 |
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