CN102766090A - Purification method of 3-(3-quinolyl)-2-propenyl-1-tert-butyl carbonate - Google Patents
Purification method of 3-(3-quinolyl)-2-propenyl-1-tert-butyl carbonate Download PDFInfo
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- CN102766090A CN102766090A CN2011101173428A CN201110117342A CN102766090A CN 102766090 A CN102766090 A CN 102766090A CN 2011101173428 A CN2011101173428 A CN 2011101173428A CN 201110117342 A CN201110117342 A CN 201110117342A CN 102766090 A CN102766090 A CN 102766090A
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- quinolyl
- tert
- propenyl
- butyl carbonate
- propylene
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Abstract
The invention belongs to the technical field of a purification method of 3-(3-quinolyl)-2-propenyl-1-tert-butyl carbonate. The purification method of 3-(3-quinolyl)-2-propenyl-1-tert-butyl carbonate comprises the following steps of: dissolving 3-(3-quinolyl)-2-propenyl-1-tert-butyl carbonate by the use of ethyl acetate, adding a proper amount of hexane, heating, and filtering by the use of silica gel. According to the invention, the 3-(3-quinolyl)-2-propenyl-1-tert-butyl carbonate crude product only needs to be dissolved in an appropriate solvent, is slightly heated and is finally filtered by the use of a few silica gel. The purification method is simple and rapid, has a good effect, and is suitable for industrial application.
Description
Technical field
The invention belongs to the purification process technical field of 3-(3-quinolyl)-2-propylene-1-alcohol carbonic acid tertiary butyl ester.
Background technology
3-(3-quinolyl)-2-propylene-1-alcohol carbonic acid tertiary butyl ester is a disclosed compound in patent US2003199696A1.The method for preparing 3-(3-quinolyl)-2-propylene-1-alcohol carbonic acid tertiary butyl ester is a raw material with the 3-bromoquinoline generally, can be through two kinds of method preparations.
Method one: 3-bromoquinoline (I) obtains formula (II) compound with propynol through the Sonogashira reaction earlier; Again triple bond is reduced into two keys and obtains formula (III) compound, last and tert-Butyl dicarbonate prepared in reaction 3-(3-quinolyl)-2-propylene-1-alcohol carbonic acid tertiary butyl ester (IV).
In aforesaid method (document US 2003199696A1), 3-(3-quinolyl)-2-propylene-1-alcohol carbonic acid tertiary butyl ester need just can make purer product through column chromatography, and inconvenient operation has also increased cost.
Summary of the invention
The object of the invention just is to address the above problem, and a kind of 3-(3-quinolyl)-2-propylene-1-alcohol carbonic acid tertiary butyl ester purification process that is suitable for suitability for industrialized production is provided.
For reaching above-mentioned purpose, the technical scheme that the present invention takes is following:
3-(3-quinolyl)-2-propylene-1-alcohol carbonic acid tertiary butyl ester purification process; This method is with ETHYLE ACETATE 3-(3-quinolyl)-2-propylene-1-alcohol carbonic acid tertiary butyl ester to be dissolved earlier, adds an amount of normal hexane then, heating; Use silica gel to filter, promptly obtain pure target compound.
In the above-mentioned purification process, the add-on of normal hexane and the volume ratio of ETHYLE ACETATE are normal hexane: ETHYLE ACETATE=1: 3 to 10: 1.The temperature of two kinds of solvent adding post-heating is preferably at 15 ℃ to 75 ℃.
3-(3-quinolyl)-2-propylene-1-alcohol carbonic acid tertiary butyl ester bullion can be according to other existing method preparations such as document US 2003199696A1.
Beneficial effect of the present invention:
3-of the present invention (3-quinolyl)-2-propylene-1-alcohol carbonic acid tertiary butyl ester purification process only needs 3-(3-quinolyl)-2-propylene-1-alcohol carbonic acid tertiary butyl ester dissolving crude product in suitable solvent; The heating back a spot of silica gel of use detaches and gets final product a little; Method is simply quick; Effective, be suitable for industrial applications.And need in the existing method to use column chromatography just can make purer product, inconvenient operation has also increased cost.
Embodiment
The embodiment that provides is used for describing the application of preferred embodiment and the inventive method, rather than is used for limiting the present invention, only if in accompanying claims, state.
The preparation of embodiment 1:3-(3-quinolyl)-2-propine-1-alcohol
In the 2000ml reaction flask, add the 84.2g compound, 110g tert-Butyl dicarbonate, 4.8g 4-butyl ammonium hydrogen sulfate; Add methylene dichloride 1000ml then, it is cooled to 0-5 ℃ with ice-water bath, drip the 25%NaOH solution of 220ml then; 40min drips off, and keeps 25-30 ℃ of reaction 4h, then reaction solution is diluted with the 500ml methylene dichloride; With washing (2x800ml), wash with the 600ml saturated sodium bicarbonate more earlier, the 600ml saturated sodium-chloride is washed; Behind anhydrous sodium sulfate drying, suction filtration, the filtrating evaporate to dryness obtains dark red dark oil thing 124.4g (95.9%).
Embodiment 2
The oily matter that embodiment 1 makes is used the 150ml acetic acid ethyl dissolution, add the 450ml normal hexane again, be heated to boiling; The black dope is arranged, filter through the sand core funnel that is lined with a small amount of silica gel while hot, the black dope of staying in the bottle is used the 150ml acetic acid ethyl dissolution again; Add the 450ml normal hexane, stir, have more insoluble red solid to occur; With its together the sand core funnel through the front filter, use the 600ml normal hexane again: the solvent of ETHYLE ACETATE=3: 1 is washed, and will filtrate, it is dried to concentrate; Get light red oil, room temperature is placed and moments later is frozen into faint yellow solid 120.6g (93%).
Embodiment 3
The oily matter that embodiment 1 makes is used the 150ml acetic acid ethyl dissolution, add the 1200ml normal hexane again, be heated to boiling; The black dope is arranged, filter through the sand core funnel that is lined with a small amount of silica gel while hot, the black dope of staying in the bottle is used the 150ml acetic acid ethyl dissolution again; Add the 1200ml normal hexane, stir, have more insoluble red solid to occur; With its together the sand core funnel through the front filter, use the 600ml normal hexane again: the solvent of ETHYLE ACETATE=8: 1 is washed, and will filtrate, it is dried to concentrate; Get light red oil, room temperature is placed and moments later is frozen into faint yellow solid 119.8g (92.4%).
Embodiment 4
The oily matter that embodiment 1 makes is used the 200ml acetic acid ethyl dissolution, add the 200ml normal hexane again, be heated to boiling; The black dope is arranged, filter through the sand core funnel that is lined with a small amount of silica gel while hot, the black dope of staying in the bottle is used the 200ml acetic acid ethyl dissolution again; Add the 200ml normal hexane, stir, have more insoluble red solid to occur; With its together the sand core funnel through the front filter, use the 600ml normal hexane again: the solvent of ETHYLE ACETATE=1: 1 is washed, and will filtrate, it is dried to concentrate; Get light red oil, room temperature is placed and moments later is frozen into faint yellow solid 122g (94%).
By means of above description and the for example clear the present invention of embodiment.More than describe and should illustrate as non-limiting, because for a person skilled in the art, many variations of making in view of the above are conspicuous.Should think that all these variations should be included within the scope and essence of accompanying claims.
Can be to the combination of the inventive method described herein, operation and layout are replaced, and do not deviate from inventive concept and the scope that is limited claim.
Claims (3)
1.3-(3-quinolyl)-2-propylene-1-alcohol carbonic acid tertiary butyl ester purification process, this method are with ETHYLE ACETATE 3-(3-quinolyl)-2-propylene-1-alcohol carbonic acid tertiary butyl ester to be dissolved earlier, add an amount of normal hexane then, heating uses silica gel to filter.
2. 3-as claimed in claim 1 (3-quinolyl)-2-propylene-1-alcohol carbonic acid tertiary butyl ester purification process, it is characterized in that: the add-on of normal hexane and the volume ratio of ETHYLE ACETATE are 1: 3-10: 1.
3. 3-as claimed in claim 1 (3-quinolyl)-2-propylene-1-alcohol carbonic acid tertiary butyl ester purification process, it is characterized in that: the TR of heating is at 15 ℃ to 75 ℃.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011101173428A CN102766090A (en) | 2011-05-06 | 2011-05-06 | Purification method of 3-(3-quinolyl)-2-propenyl-1-tert-butyl carbonate |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011101173428A CN102766090A (en) | 2011-05-06 | 2011-05-06 | Purification method of 3-(3-quinolyl)-2-propenyl-1-tert-butyl carbonate |
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| CN102766090A true CN102766090A (en) | 2012-11-07 |
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| CN2011101173428A Pending CN102766090A (en) | 2011-05-06 | 2011-05-06 | Purification method of 3-(3-quinolyl)-2-propenyl-1-tert-butyl carbonate |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1444562A (en) * | 2000-05-30 | 2003-09-24 | 明治制果株式会社 | Rice blast control agents |
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2011
- 2011-05-06 CN CN2011101173428A patent/CN102766090A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1444562A (en) * | 2000-05-30 | 2003-09-24 | 明治制果株式会社 | Rice blast control agents |
Non-Patent Citations (1)
| Title |
|---|
| 金洁 等: "新型大环内酯类抗生素塞红霉素关键中间体的合成", 《中国新药杂志》, vol. 13, no. 11, 31 December 2004 (2004-12-31), pages 1017 - 1019 * |
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Application publication date: 20121107 |