CN109678673A - A kind of synthetic method for the homoallylic alcohol that aryl replaces - Google Patents
A kind of synthetic method for the homoallylic alcohol that aryl replaces Download PDFInfo
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- CN109678673A CN109678673A CN201811349914.3A CN201811349914A CN109678673A CN 109678673 A CN109678673 A CN 109678673A CN 201811349914 A CN201811349914 A CN 201811349914A CN 109678673 A CN109678673 A CN 109678673A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B41/00—Formation or introduction of functional groups containing oxygen
- C07B41/02—Formation or introduction of functional groups containing oxygen of hydroxy or O-metal groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
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Abstract
The present invention relates to compound preparations, belong to organic synthesis field.The synthetic method for disclosing a kind of homoallylic alcohol that aryl replaces under the action of copper catalyst, ligand and alkali, is reacted using aryl boron compound and alkenyl epoxy as raw material in solvent, obtains the homoallylic alcohol compound that there is E- configuration aryl to replace.Has many advantages, such as the problems such as synthetic route is short high with reaction yield, and the homoallylic alcohol route for solving current synthesizing aryl substitution is long, severe reaction conditions, overall yield of reaction is low using the homoallylic alcohol that the aryl of the method for the present invention synthesis replaces.This reaction system feed way is simple simultaneously, and reaction reagent stablizes air and water, more convenient in actual operation.Conversion zone and stereoselectivity are high, no coupling product, and separation is simple.The reaction simultaneously can be compatible with the group of some sensitivities well, and functional group compatibility is superior.
Description
Technical field
The present invention relates to compound preparations, belong to organic synthesis field.The homoallylic alcohol replaced more particularly to a kind of aryl
Synthetic method.
Background technique
Alcohol is a kind of important organic compound, is widely present in the industries such as drug, food.And alcohol is also a kind of
Important organic synthesis intermediate can be converted to organic conjunction such as alkyl halide, alkyl sulfonic ester by simply chemically reacting
Cheng Zi, and the cross-coupling reaction of various metals catalysis is participated in, for constructing C-C key and C- heterodesmic.
Homoallylic alcohol as a kind of special alcohol compound containing unsaturated hydrocarbons, in organic synthesis be it is a kind of very
Important intermediate is needed in the reaction of many types using homoallylic alcohol structural framework.And the homoallylic alcohol that aryl replaces
It is had important application in organic synthesis as a kind of special homoallylic alcohol.Its tetrahydro furan that can be converted to aryl substitution
It mutters, β-chloro, Beta-bromo, β-fluoro tetrahydrofuran.Therefore the synthetic method one of efficient, convenient, easy-operating alkylol is developed
It is directly the emphasis of people's research.
Aryl replaces homoallylic alcohol to have important application, and there are mainly three types of paths for forefathers' synthetic method.Formula (1) described side
Method is Sigman and Suero Liang Ge group etc. respectively in J.Am.Chem.Soc.2012,134,11408-11411 and
Angew.Chem.Int.Ed.2017, the method for 56,1610-1613 reports, first using 4- bromobutanol in fert-butyidimethylsilyl
Protect exposed alcoholic extract hydroxyl group under the conditions of chlorosilane, then with triphenyl phosphorus (PPh3) reaction obtain quaternary alkylphosphonium salt intermediate, the intermediate
(- 20 DEG C to -70 DEG C) under cryogenic, Wittig reaction occurs for (butyl lithium) and benzaldehyde under basic conditions, is protected
Aryl replace homoallylic alcohol.Protecting group finally is sloughed under the conditions of tetrabutyl ammonium fluoride (TBAF), obtains aryl substitution
Homoallylic alcohol.The homoallylic alcohol route that synthesizing aryl replaces in this way is longer, and severe reaction conditions, reaction temperature is low, and needs
Highly basic is used, certain economy and manpower waste are caused.
Reaction route is long, severe reaction conditions
The method of another synthesizing aryl homoallylic alcohol mainly passes through olefin metathesis reaction, if formula (2) is Anderson
In Angew.Chem.Int.Ed.2013,52,9139-9143 reports are replaced people by olefin metathesis reaction synthesizing aryl
The example of homoallylic alcohol is needed using Grubbs catalyst, and this catalyst is expensive.It is needed simultaneously using styrene original
Material, but commercialized substituted phenylethylene be it is fewer, this just give synthesize it is a variety of replace types aryl homoallylic alcohols bring
Difficulty is restricted its synthesis value.
Grubbs expensive catalyst, commercialized substituted phenylethylene are seldom
A kind of last method of synthesizing aryl homoallylic alcohol mainly passes through Sonogashira coupling reaction and prepares, such as formula (3)
It is Chen group in Chem.Commun.2016,52,4537-4540 reports are taken by Sonogashira reaction synthesizing aryl
The example of the homoallylic alcohol in generation.The generation Sonogashira reaction of aryl halide and alkynes butanol first, reuses going back for strong reducing property
Former agent (lithium aluminium hydride reduction, AlLiH4) alkynes is restored, due to use stronger reducing agent, one is brought to functional group compatibility
Foregone conclusion limit.And lithium aluminium hydride reduction reactivity is high, and reaction need to control reaction temperature.
Two-step reaction needs just with strong reductant LiAlH4, reactivity is high, and strict control reaction temperature is troublesome in poeration
Although the homoallylic alcohol that can be replaced by three kinds of example synthesizing aryls above, each method all exist centainly
Limitation, 1 route of method is long, severe reaction conditions.2 expensive catalyst of method, reaction raw materials source are few.Method 3 also needs
Two step process, while needing using strong reductant, troublesome in poeration, strict control reaction carries out at low temperature.
The homoallylic alcohol that aryl replaces has very big demand in material, organic synthesis and pharmaceuticals industry, current existing conjunction
The method of the homoallylic alcohol replaced at aryl all has some disadvantages.So efficient, economic, convenient and fast synthesizing aryl replaces
Homoallylic alcohol be a problem in chemical synthesis.
Summary of the invention
That there are routes is long for the homoallylic alcohol that aryl replaces by the present invention, and raw material sources are limited, expensive catalyst, reaction item
The problems such as part is harsh, provide it is a kind of reaction using simple cheap copper catalyst, raw material sources it is extensive, reaction condition is mild, official
Good compatibility can be rolled into a ball, reaction route is short, it is only necessary to which the homoallylic alcohol for preparing aryl substitution based on copper catalysis of single step reaction closes
At method.
In order to solve the above technical problems, the present invention adopts the following technical scheme: a kind of homoallylic alcohol for preparing aryl substitution
Synthetic method, it is characterised in that: using aryl boron compound and alkenyl epoxy as raw material, in the work of copper catalyst, ligand and alkali
It under, is reacted in solvent by following reaction equations, obtains the homoallylic alcohol replaced with the E- configuration aryl of logical formula (I)
Close object:
Wherein R is a plurality of types of substituent groups；
The catalyst is stannous chloride；
Wherein a plurality of types of substituent groups of R；
The catalyst is stannous chloride；
The ligand is phosphorus ligand, 1,3- diones ligand, dinitrogen class ligand；
The solvent is dioxane, n,N-Dimethylformamide, n,N-dimethylacetamide, one in tetrahydrofuran
Kind；
The aryl boron ester is aryl neopentyl glycol ester.
Preferably, the alkali is one of lithium methoxide, tert-butyl alcohol lithium.
Preferably, the amount of the substance of the alkali is 2.5 times of the amount of the substance of alkenyl epoxy.
Preferably, the amount of the substance of the molecule aryl neopentyl glycol ester is 2 times of the amount of the substance of alkenyl epoxy.
Preferably, the amount of the substance of the copper catalyst is the 10% of the amount of the substance of alkenyl epoxy.
Preferably, the amount of the substance of the ligand is the 15% of the amount of the substance of alkenyl epoxy.
Preferably, reaction temperature in a solvent is 60 DEG C, reaction time 10h.
Compared to the method for the homoallylic alcohol that existing aryl replaces, the high allyl replaced using the method for the present invention synthesizing aryl
Alcohol reaction route is short, it is only necessary to which a step, catalyst is cheap, and raw material is easy to get, and does not need using strong reducing property catalyst, synthesis is economical
Value is high, and raw material sources are wide, and reaction yield is high.This reaction system feed way is simple simultaneously, without using to moisture and air
Sensitive reagent, it is more convenient in actual use.In addition, this reaction system reaction condition is mild, can be compatible with well
Sensitive group, this be in reaction system before it is difficult to realize, provided for the homoallylic alcohol that aryl replaces efficient, just
Prompt, economic preparation method.
Detailed description of the invention
Fig. 1 is the nuclear magnetic resonance spectroscopy for the homoallylic alcohol 1 that aryl prepared by the present invention replaces；
Fig. 2 is the carbon-13 nmr spectra for the homoallylic alcohol 1 that aryl prepared by the present invention replaces；
Fig. 3 is the nuclear magnetic resonance spectroscopy for the homoallylic alcohol 2 that aryl prepared by the present invention replaces；
Fig. 4 is the carbon-13 nmr spectra for the homoallylic alcohol 2 that aryl prepared by the present invention replaces；
Fig. 5 is the nuclear magnetic resonance spectroscopy for the homoallylic alcohol 3 that aryl prepared by the present invention replaces；
Fig. 6 is the carbon-13 nmr spectra for the homoallylic alcohol 3 that aryl prepared by the present invention replaces；
Fig. 7 is the nuclear magnetic resonance spectroscopy for the homoallylic alcohol 4 that aryl prepared by the present invention replaces；
Fig. 8 is the carbon-13 nmr spectra for the homoallylic alcohol 4 that aryl prepared by the present invention replaces；
Fig. 9 is the nuclear magnetic resonance spectroscopy for the homoallylic alcohol 5 that aryl prepared by the present invention replaces；
Figure 10 is the Enantiomeric excess for the homoallylic alcohol 5 that aryl prepared by the present invention replaces
Figure 11 is the carbon-13 nmr spectra for the homoallylic alcohol 5 that aryl prepared by the present invention replaces；
Figure 12 is the nuclear magnetic resonance spectroscopy for the homoallylic alcohol 6 that aryl prepared by the present invention replaces；
Figure 13 is the carbon-13 nmr spectra for the homoallylic alcohol 6 that aryl prepared by the present invention replaces；
Figure 14 is the nuclear magnetic resonance spectroscopy for the homoallylic alcohol 7 that aryl prepared by the present invention replaces；
Figure 15 is the Enantiomeric excess for the homoallylic alcohol 7 that aryl prepared by the present invention replaces；
Figure 16 is the carbon-13 nmr spectra for the homoallylic alcohol 7 that aryl prepared by the present invention replaces；
Figure 17 is the nuclear magnetic resonance spectroscopy for the homoallylic alcohol 8 that aryl prepared by the present invention replaces；
Figure 18 is the carbon-13 nmr spectra for the homoallylic alcohol 8 that aryl prepared by the present invention replaces；
Figure 19 is the nuclear magnetic resonance spectroscopy for the homoallylic alcohol 9 that aryl prepared by the present invention replaces；
Figure 20 is the carbon-13 nmr spectra for the homoallylic alcohol 9 that aryl prepared by the present invention replaces；
Figure 21 is the nuclear magnetic resonance spectroscopy for the homoallylic alcohol 10 that aryl prepared by the present invention replaces；
Figure 22 is the carbon-13 nmr spectra for the homoallylic alcohol 10 that aryl prepared by the present invention replaces；
Figure 23 is the nuclear magnetic resonance spectroscopy for the homoallylic alcohol 11 that aryl prepared by the present invention replaces；
Figure 24 is the carbon-13 nmr spectra for the homoallylic alcohol 11 that aryl prepared by the present invention replaces；
Figure 25 is the nuclear magnetic resonance spectroscopy for the homoallylic alcohol 12 that aryl prepared by the present invention replaces；
Figure 26 is the carbon-13 nmr spectra for the homoallylic alcohol 12 that aryl prepared by the present invention replaces；
Figure 27 is the nuclear magnetic resonance spectroscopy for the homoallylic alcohol 13 that aryl prepared by the present invention replaces；
Figure 28 is the carbon-13 nmr spectra for the homoallylic alcohol 13 that aryl prepared by the present invention replaces；
Specific embodiment
Technical solution of the present invention is described further below by specific embodiment:
The reaction equation of embodiment 1, the embodiment is as follows:
(1) under air, stannous chloride (CuCl, 10mol%), tetramethylethylenediamine (TMEDA, 15mol%), the tert-butyl alcohol
Lithium (LiOtBu, 2.5eq), meta-methoxy-aryl neopentyl glycol boron ester (2eq) be added to one with branch pipe, containing the close of magneton
It seals in reaction tube, reaction tube pumping rushes argon gas three times.Under protection of argon gas, 0.6mL N, N- dimethyl formyl are added into reaction tube
Amine is then added vinyl epoxy (0.25mmol) into reaction solution under protection of argon gas, stoppers piston, be placed in 60 DEG C of oil bath pans
In be stirred to react 10 hours.
(2) saturated ammonium chloride is added in resulting material in step (1) to be quenched, ethyl acetate is added and is sufficiently mixed, with short silicon
After rubber column gel column filters out solid residue, retain organic phase.
(3) solvent in organic phase obtained in spinning step (2), obtains crude product, is then slightly produced with silica gel column purification
Object.Eluant, eluent is petroleum ether and ethyl acetate mixture, separation yield 86%, product purity 100%.
Embodiment 2
The reaction equation of the embodiment is as follows:
(1) under air, stannous chloride (CuCl, 10mol%), tetramethylethylenediamine (TMEDA, 15mol%), the tert-butyl alcohol
Lithium (LiOtBu, 2.5eq), a sealing with branch pipe, containing magneton is added to chlorine aryl neopentyl glycol boron ester (2eq) and is reacted
Guan Zhong, reaction tube pumping rush argon gas three times.Under protection of argon gas, 0.6mL n,N-Dimethylformamide is added into reaction tube, connects
Under protection of argon gas be added vinyl epoxy (0.25mmol) into reaction solution, stopper piston, be placed in 60 DEG C of oil bath pans and stir
Mix reaction 10 hours.
(2) saturated ammonium chloride is added in resulting material in step (1) to be quenched, ethyl acetate is added and is sufficiently mixed, with short silicon
After rubber column gel column filters out solid residue, retain organic phase.
(3) solvent in organic phase obtained in spinning step (2), obtains crude product, is then slightly produced with silica gel column purification
Object.Eluant, eluent is petroleum ether and ethyl acetate mixture, separation yield 82%, product purity 100%.
Embodiment 3
The reaction equation of the embodiment is as follows:
(1) under air, stannous chloride (CuCl, 10mol%), tetramethylethylenediamine (TMEDA, 15mol%), the tert-butyl alcohol
Lithium (LiOtBu, 2.5eq), a sealing with branch pipe, containing magneton is added to bromine aryl neopentyl glycol boron ester (2eq) and is reacted
Guan Zhong, reaction tube pumping rush argon gas three times.Under protection of argon gas, 0.6mL n,N-Dimethylformamide is added into reaction tube, connects
Under protection of argon gas be added vinyl epoxy (0.25mmol) into reaction solution, stopper piston, be placed in 60 DEG C of oil bath pans and stir
Mix reaction 10 hours.
(2) saturated ammonium chloride is added in resulting material in step (1) to be quenched, ethyl acetate is added and is sufficiently mixed, with short silicon
After rubber column gel column filters out solid residue, retain organic phase.
(3) solvent in organic phase obtained in spinning step (2), obtains crude product, is then slightly produced with silica gel column purification
Object.Eluant, eluent is petroleum ether and ethyl acetate mixture, separation yield 83%, product purity 100%.
Embodiment 4
The reaction equation of the embodiment is as follows:
(1) under air, stannous chloride (CuCl, 10mol%), tetramethylethylenediamine (TMEDA, 15mol%), the tert-butyl alcohol
Lithium (LiOtBu, 2.5eq), a sealing reaction tube with branch pipe, containing magneton is added to furans neopentyl glycol boron ester (2eq)
In, reaction tube pumping rushes argon gas three times.Under protection of argon gas, 0.6mL n,N-Dimethylformamide is added into reaction tube, then
Vinyl epoxy (0.25mmol) is added under protection of argon gas into reaction solution, stoppers piston, is placed in 60 DEG C of oil bath pans and stirs
Reaction 10 hours.
(2) 1-2mL ethyl acetate is added in resulting material in step (1), 2h is stirred at room temperature, filtered out with short silicagel column solid
After body residue, retain organic phase.
(3) solvent in organic phase obtained in spinning step (2), obtains crude product, is then slightly produced with silica gel column purification
Object.Eluant, eluent is petroleum ether and ethyl acetate mixture, separation yield 80%, product purity 100%.
The nuclear magnetic resonance map and data for the homoallylic alcohol that the aryl being prepared replaces are as shown in table 1 and attached drawing.
Table 1
The amount and reaction condition of each substance used carry out laboratory exploration with embodiment, to illustrate technical solution of the present invention
With good functional group compatibility, each expansion reaction equation is as follows:
The above has been described in detail, described above, is only a preferred embodiment of the present invention, when cannot
Limit the application practical range, i.e., it is all according to the made equivalent changes and modifications of the application range, it should still belong to covering scope of the present invention
It is interior.
Claims (7)
1. a kind of synthetic method for the homoallylic alcohol that aryl replaces, it is characterised in that: be with aryl boron compound and alkenyl epoxy
Raw material is reacted in solvent by following reaction equations under the action of copper catalyst, ligand and alkali, obtains having logical formula (I)
E- configuration aryl replace homoallylic alcohol compound:
Wherein R is a plurality of types of substituent groups；
The catalyst is stannous chloride；
The ligand is one of triphenyl phosphorus, dinitrogen class ligand, diketone class ligand；
The solvent is one of dioxane, n,N-Dimethylformamide, n,N-dimethylacetamide, tetrahydrofuran；
The boron ester is aryl neopentyl glycol boron ester.
2. the synthetic method for the homoallylic alcohol that a kind of aryl according to claim 1 replaces, it is characterised in that: the alkali is
One of tert-butyl alcohol lithium, lithium methoxide, cesium carbonate.
3. the synthetic method for the homoallylic alcohol that a kind of aryl according to claim 2 replaces, it is characterised in that: the alkali
The amount of substance is 2.5 times of the amount of the substance of alkenyl epoxide.
4. the synthetic method for the homoallylic alcohol that a kind of aryl according to claim 1 replaces, it is characterised in that: the molecule
The amount of the substance of aryl boron ester is 2 times of the amount of the substance of alkenyl epoxy.
5. the synthetic method for the homoallylic alcohol that a kind of aryl according to claim 1 replaces, it is characterised in that: the copper is urged
The amount of the substance of agent is the 10% of the amount of the substance of alkenyl epoxy.
6. the synthetic method for the homoallylic alcohol that a kind of aryl according to claim 1 replaces, it is characterised in that: the ligand
Substance amount be alkenyl epoxy substance amount 15%.
7. the synthetic method for the homoallylic alcohol that a kind of aryl according to claim 1 replaces, it is characterised in that: in a solvent
Reaction temperature be 60 DEG C, reaction time 10h.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110724033A (en) * | 2019-10-19 | 2020-01-24 | 滁州学院 | Method for preparing alcohol by Suzuki reaction without exogenous base |
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| CN107602320A (en) * | 2017-10-18 | 2018-01-19 | 滁州学院 | It is a kind of that the synthetic method for preparing three substituted olefines is catalyzed based on nickel |
| CN108530389A (en) * | 2018-05-22 | 2018-09-14 | 东北师范大学 | A kind of preparation method of 2- aryl cyclopropyls amine compounds |
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Patent Citations (2)
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|---|---|---|---|---|
| CN107602320A (en) * | 2017-10-18 | 2018-01-19 | 滁州学院 | It is a kind of that the synthetic method for preparing three substituted olefines is catalyzed based on nickel |
| CN108530389A (en) * | 2018-05-22 | 2018-09-14 | 东北师范大学 | A kind of preparation method of 2- aryl cyclopropyls amine compounds |
Non-Patent Citations (1)
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| LU XIAOYU等: "Cu-Catalyzed cross-coupling reactions of epoxides with organoboron compounds", 《CHEMICAL COMMUNICATIONS》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110724033A (en) * | 2019-10-19 | 2020-01-24 | 滁州学院 | Method for preparing alcohol by Suzuki reaction without exogenous base |
| CN110724033B (en) * | 2019-10-19 | 2023-06-09 | 滁州学院 | Method for preparing alcohol by using Suzuki reaction without exogenous alkali |
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