CN107805232A - A kind of synthetic method of the derivative containing thiomethylfuran - Google Patents
A kind of synthetic method of the derivative containing thiomethylfuran Download PDFInfo
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- 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
- C07D307/56—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
The invention discloses a kind of synthetic method of derivative containing thiomethylfuran, this method is by acetophenone compounds and dimethyl sulfoxide (DMSO), the one pot reaction in the presence of simple substance iodine catalyst and potassium persulfate oxidation agent, obtains derivative containing thiomethylfuran；This method enriches furan derivatives species, provides more intermediates for pharmaceutical synthesis, and raw material sources are wide, step is simple, reaction condition is gentle, high income, are advantageous to industrialized production.
Description
Technical field
The present invention relates to a kind of synthetic method of substituted furan, and more particularly to one kind is by acetophenone compounds and dimethyl
The method that sulfoxide generates furan derivatives under iodine catalytic action by potassium persulfate oxidation single step reaction, belongs in medicine
Mesosome synthesizes field.
Background technology
Furan derivatives are organic or pharmaceutical synthesis a kind of important raw material or intermediate.In the prior art, it is relative complex
Furan derivatives medicine class often relies on to be extracted from natural plants, such as Chinese patent (publication number：101830871A) disclose
A kind of method that furan derivatives are extracted in fruit from Snakegourd Fruit, is specifically extracted, chromatographic isolation using ethanol, can be used for
The furan derivatives medicine of the various diseases caused by complement system transition activation is treated, it is this to rely on extracted form natural plant furans
The method cost of derivative is high, and yield is low, strong to natural resources dependent form.And simple furan derivatives can utilize furans former
Expect, to synthesize, mainly have aromatic ring property using furan nucleus, by carrying out the parental materials such as halogenation, nitrification, sulfonation, acylation to it
Reaction, obtains different substitution products, and such as document, (" synthesis of 2- acetyl furans ", petrochemical industry, 2008, volume 37 increased
Periodical, 328-330) disclose a kind of 2- acetyl furans that can be used for pharmaceutical intermediate and food additives, mainly using iodine,
Phosphoric acid etc. is used as catalyst, and 2- acetyl furans are synthesized by acetic anhydride and furans.And can also by simple furan derivatives
Further modified, it is hereby achieved that relative complex furan derivatives, such as document, (" synthesis of 2- furan boronic acids is ground
Study carefully ", Hebei University of Science and Technology's journal, in April, 2012, the 2nd phase of volume 33,103-106 pages) disclose by 2- bromines furans and boric acid three
Butyl ester is raw material, has synthesized 2- furan boronic acids using n-BuLi method, 2- furan boronic acids can be anti-by Suzuki cross-couplings
SP should be built2Type C-C singly-bounds, it is hereby achieved that the furan derivatives of the substituted radical such as various aromatic rings.These pass through in furan
Muttering directly is influenceed by synthesizing the method for furan derivatives the methods of substitution reaction by furan nucleus electronic effect on ring, is substituted
The quantity of base group modification and position are limited.At present, also there is the synthesis that furan derivatives are realized by directly synthesizing furan nucleus, and
Complicated substituted radical can be directly introduced from raw material, more classical is that Paal-Knorr reactions are used for synthesizing furans derivative
Thing, as Isosorbide-5-Nitrae-dicarbonyl compound is dehydrated under anhydrous acid condition, Furan and its derivatives are generated, reaction equation is as follows：Wherein, the tert-butyl group can also use other groups to replace, it is hereby achieved that 2
Position and the furan derivatives of 5 substitutions.But this method is difficult to obtain in itself using Isosorbide-5-Nitrae-cyclohexadione compounds, limits the party
The application of method.
The content of the invention
The shortcomings that existing for the methods of existing synthesis furan derivatives, the purpose of the present invention be to provide it is a kind of by
Acetophenone compounds and dimethyl sulfoxide (DMSO) generate furans under iodine catalytic action by potassium persulfate oxidation single step reaction
The method of derivative, this method enrich furan derivatives species, and more intermediates, and raw material sources are provided for pharmaceutical synthesis
Extensively, step is simple, reaction condition is gentle, high income, is advantageous to industrialized production.
In order to realize above-mentioned technical purpose, the invention provides a kind of synthetic method of derivative containing thiomethylfuran, formula 1
Acetophenone compounds and dimethyl sulfoxide (DMSO), the one pot reaction in the presence of simple substance iodine catalyst and potassium persulfate oxidation agent, are obtained
The furan derivatives of formula 2；
Wherein, R is hydrogen, halogenic substituent, trifluoromethyl, nitro, alkyl, alkoxy or methyl mercapto.
Preferable scheme, substituted-phenyl in acetophenone compounds is for example adjacent// p-bromophenyl, neighbour// to chlorobenzene
Base, neighbour/to trifluoromethyl, neighbour// p-methylphenyl, neighbour/m-nitro base, neighbour/to methoxyl group, to methyl mercapto, to tert-butyl benzene
Base etc..Acetophenone compounds containing these substituents can obtain higher receipts during corresponding furan derivatives are synthesized
Rate.
Preferable scheme, concentration of the acetophenone compounds in dimethyl sulfoxide (DMSO) are 0.1~1mol/L；More preferably
For 0.2~0.3mol/L.
Preferable scheme, the mole of the tetraalkylammonium iodides are the 20~40% of acetophenone compounds mole；
More preferably 25~35%.
Preferable scheme, the mole of the potassium persulfate oxidation agent are 2~3 times of acetophenone compounds mole.
More preferably it is 2~2.5 times.
Preferable scheme, the condition of the reaction：Reaction temperature is 90~140 DEG C, and the reaction time is 5~11h.Further
Preferable reaction condition：Reaction temperature is 100~130 DEG C, and the reaction time is 6~10h；Preferred reaction condition：Reaction temperature
Spend for 115~125 DEG C, the reaction time is 7~9h.
Iodine is used as catalyst in technical scheme, and potassium peroxydisulfate is used as oxidant.Furan
Derivative of muttering is formed by two molecule acetophenone compounds and a molecule dimethyl sulfoxide (DMSO) by cyclisation, wherein a molecule acetophenone
The methyl of the acetyl group of class compound, the methyl of a molecule acetophenone compounds and a molecule dimethyl sulfoxide (DMSO) is in iodine
It is cyclized under catalyst and potassium persulfate oxidation agent effect, so as to obtain 2,3 and 5 simultaneously-substituted furan derivatives.
Dimethyl sulfoxide (DMSO) has the function that two important, on the one hand organic solvents good as dissolubility in technical solution of the present invention, can
To improve reaction efficiency, cyclisation on the other hand is participated in as reaction substrate, one methyl, another methyl is in the form of methyl mercapto
Modification is on the furan nucleus of formation.
Compared with the prior art, the advantageous effects that technical scheme is brought：
1) technical solution of the present invention realizes that carrying out oxidative cyclization with dimethyl sulfoxide (DMSO) by acetophenone compounds obtains first
Furan derivatives, a kind of new thought is provided for synthesis furan derivatives.
2) technical scheme uses conventional acetophenone compounds and dimethyl sulfoxide (DMSO) as raw material, relatively existing
Some 1,4- cyclohexadione compounds raw materials have the advantages of cost is low.
3) technical scheme step is simple, reaction condition is gentle, and furan derivatives can be realized by one kettle way
Synthesis, and reaction yield is high, is advantageous to mass produce.
4) aryl and methyl mercapto that the furan derivatives of technical scheme synthesis include are easy modification group again,
There is obvious advantage as nitrofurans synthetic intermediate.
Brief description of the drawings
【Fig. 1】For the 1H NMR spectras of furan derivatives in embodiment 1；
【Fig. 2】For the 13C NMR spectras of furan derivatives in embodiment 1；
【Fig. 3】For the 1H NMR spectras of furan derivatives in embodiment 2；
【Fig. 4】For the 13C NMR spectras of furan derivatives in embodiment 2.
Embodiment
Following examples are intended to further illustrate present invention, rather than the protection model of limitation the claims in the present invention
Enclose.
The substrate raw material being related in following examples, and solvent etc. are commercially available commercial product (AR), and
And it is not further purified.
Product separation uses chromatography, chromatographic column silica gel (300-400 mesh).
1H NMR (400MHz), 13C NMR (100MHz), with CDCl3For solvent, using TMS as internal standard.
Multiplicity is defined as follows：S (unimodal)；D (doublet)；T (triplet)；Q (quartet) and m (multiplet).Coupling
Constant J (hertz).
Condition optimizing is tested：Optimum reaction condition is found by following control experiment group：With acetophenone and dimethyl sulfoxide (DMSO)
For reaction raw materials, while excess dimethyl sulfoxide is illustrated, specific reaction is as follows as reaction dissolvent：
Weigh catalyst, acetophenone, oxidant to be placed in 25mL reaction tube, add dimethyl sulfoxide (DMSO) as molten
Agent, mixed liquor are heated under the conditions of certain temperature in air atmosphere, stirring reaction.Reaction solution is cooled to room temperature, using acetic acid
Ethyl ester (10mL) is diluted to reaction solution, washes (5mL), reaction solution is extracted using ethyl acetate (5mL × 3), is extracted
Organic phase after taking is dried using anhydrous sodium sulfate, filtering, is then spin-dried for solvent with Rotary Evaporators.Thing after concentration
Matter carries out separating-purifying (eluant, eluent is petrol ether/ethyl acetate) using silica gel column chromatography, obtains final product.
The reaction condition of control experiment group 1~11:Acetophenone (0.5mmol), DMSO (2.0mL), catalyst (30mol%),
Oxidant (1.0mmol), reaction time 8h.
The DMSO (1.0mL) of control experiment group 12, other conditions are identical with experimental group 1.
The DMSO (3.0mL) of control experiment group 13, other conditions are identical with experimental group 1.
The I of control experiment group 142(10mol%), other conditions are identical with experimental group 1.
The I of control experiment group 152(50mol%), other conditions are identical with experimental group 1.
As can be seen that reacting equal energy under the catalysis such as iodine, TBAB, TBAC, KI in control experiment group 1~4 from table
It is smoothed out, but iodine is compared to TBAB, TBAC etc. and KI has more preferable catalytic activity, the furans accordingly obtained
Derivative yield is higher.
It is can be seen that from table in control experiment group 1 and 5~9 except persulfate can carry out reaction, other conventional oxygen
Agent such as hydrogen peroxide, oxygen, peroxide TBHP etc. can not realize the synthesis of furan derivatives, and in persulfate, with
The best results of potassium peroxydisulfate, can obtain preferable yield, and (NH4)2S2O8、KHSO5Although it can carry out reaction, yield
It is unsatisfactory.
As can be seen that reaction temperature is too high or too low in control experiment group 1 and 10~11 from table, yield all can accordingly drop
It is low, it can reach optimal reaction effect at 120 DEG C or so.
To sum up control experiment group 1~15, optimal reaction condition can be obtained：Acetophenone (0.5mmol), and methyl sulfoxide
(2mL), I2(0.15mmol), K2S2O8(1.0mmol), 120 DEG C, 8h.
Reacted according to the optimum reaction condition after above-mentioned optimization example 1 below~18：
Embodiment 1
Raw material：Acetophenone；
Target product：
Yield：83%；
1H NMR(400MHz,CDCl3):δ 8.05 (dd, J=13.7,7.6Hz, 1H), 7.65-7.59 (m, 1H), 7.53
(t, J=7.1Hz, 1H), 7.48 (t, J=7.1Hz, 1H), 7.43-7.37 (m, 1H), 7.35 (s, 1H), 2.48 (s, 1H)
13C NMR(101MHz,CDCl3):δ181.8,153.8,150.3,137.2,132.6,129.5,129.3,
129.1,128.7,128.5,126.5,124.1,118.1,18.1.
Embodiment 2
Raw material：2- bromoacetophenones；
Target product：
Yield：62%；
1H NMR(400MHz,CDCl3):δ 7.67 (t, J=7.7Hz, 1H), 7.52 (d, J=7.3Hz, 1H), 7.36
(ddd, J=26.3,15.5,7.6Hz, 2H), 7.22 (s, 1H), 2.34 (s, 1H)
13C NMR(100MHz,CDCl3):δ182.4,155.4,150.8,139.1,133.4,133.4,132.3,
131.7,131.3,130.1,129.4,127.1,127.1,123.6,123.4,120.9,120.0,18.1.
Embodiment 3
Raw material：2- trifluoromethyl acetophenones；
Target product：
Yield：50%；
1H NMR(400MHz,CDCl3):δ 7.79-7.74 (m, 1H), 7.67-7.60 (m, 2H), 7.57 (t, J=6.4Hz,
1H),7.30(s,1H),2.33(s,1H).
13C NMR(100MHz,CDCl3):δ182.4,153.6,151.3,136.4,132.2,131.5,131.3,
(130.3,130.0,129.6,129.3,128.4,127.0 q, J=5.1Hz), 126.7,126.7 (dd, J=8.7,3.9Hz),
124.9,124.7,122.7,120.8,18.0.
Embodiment 4
Raw material：2- methyl acetophenones；
Target product：
Yield：74%；
1H NMR(400MHz,CDCl3):δ 7.53 (d, J=7.5Hz, 1H), 7.40 (t, J=7.4Hz, 1H), 7.37-
7.27(m,2H),7.15(s,1H),2.43(s,2H),2.40(s,1H),2.32(s,1H).
13C NMR(100MHz,CDCl3):δ184.5,156.8,151.4,137.8,137.3,137.2,131.2,
130.9,130.7,130.2,129.8,128.4,128.3,125.5,125.1,123.7,119.,20.7,19.8,18.1.
Embodiment 5
Raw material：2- chloro-acetophenones；
Target product：
Yield：65%；
1H NMR(400MHz,CDCl3):δ 7.55 (t, J=8.4Hz, 1H), 7.46 (dd, J=19.9,8.6Hz, 1H),
7.42–7.32(m,1H),7.23(s,1H),2.35(s,1H).
13C NMR(100MHz,CDCl3):δ181.6,154.0,151.2,137.1,133.9,131.9,131.8,
131.7,131.3,131.1,130.3,130.3,129.4,128.0,126.5,123.4,121.1,18.0。
Embodiment 6
Raw material：2- nitro-acetophenones；
Target product：
Yield：64%；
1H NMR(400MHz,CDCl3):δ 8.21 (d, J=8.2Hz, 1H), 7.92 (d, J=8.1Hz, 1H), 7.82 (t, J
=7.5Hz, 1H), 7.72 (dd, J=21.5,7.4Hz, 3H), 7.59 (dd, J=15.5,7.6Hz, 2H), 7.40 (s, 1H),
2.41(s,3H).
13C NMR(100MHz,CDCl3):δ180.5,151.2,150.6,148.1,146.8,134.2,133.9,
132.7,131.4,131.2,130.4,129.2,124.7,124.4,123.0,121.6,121.4,17.9.
Embodiment 7
Raw material：2- methoxyl group benzoylformaldoximes；
Target product：
Yield：70%；
1H NMR(400MHz,CDCl3):δ 7.53 (d, J=7.5Hz, 1H), 7.47 (t, J=8.9Hz, 2H), 7.39 (dd,
J=14.8,6.8Hz, 1H), 7.14 (s, 1H), 7.06-6.94 (m, 4H), 3.86 (s, 3H), 3.83 (s, 3H), 2.32 (s,
3H).
13C NMR(100MHz,CDCl3):δ182.3,157.5,157.2,153.4,151.6,132.2,131.2,
130.7,129.69,127.8,123.1,120.4,120.2,120.2,118.4,111.6,111.3,55.8,55.5,17.8.
Embodiment 8
Raw material：3- bromoacetophenones；
Target product：
Yield：84%；
1H NMR(400MHz,CDCl3):δ 8.19 (s, 1H), 8.17 (s, 1H), 7.96 (dd, J=15.7,7.8Hz, 2H),
7.74 (d, J=7.9Hz, 1H), 7.52 (t, J=9.6Hz, 1H), 7.41 (t, J=7.9Hz, 1H), 7.38-7.30 (m, 2H),
2.49(s,3H).
13C NMR(100MHz,CDCl3):δ179.9,152.0,150.1,138.7,135.6,132.3,132.0,
131.1,130.2,130.1,129.1,127.8,124.9,123.9,122.9,122.8,119.6,17.9.
Embodiment 9
Raw material：3- methyl acetophenones；
Target product：
Yield：79%；
1H NMR(400MHz,CDCl3):δ 7.88 (d, J=8.9Hz, 1H), 7.82 (s, 1H), 7.43 (s, 1H), 7.36
(t, J=7.7Hz, 1H), 7.32 (s, 1H), 7.21 (d, J=7.1Hz, 1H), 2.46 (s, 3H), 2.43 (s, 2H)
13C NMR(100MHz,CDCl3):δ182.0,154.0,150.1,138.4,138.4,137.3,133.4,
129.9,129.8,129.4,128.6,128.3,127.1,126.5,124.1,123.8,117.8,21.5,21.4,18.1.
Embodiment 10
Raw material：3- chloro-acetophenones；
Target product：
Yield 80%；
1H NMR(400MHz,CDCl3):δ 8.04 (s, 1H), 8.00 (s, 1H), 7.91 (dd, J=13.3,7.7Hz, 2H),
(7.66 s, 1H), 7.59 (d, J=8.0Hz, 1H), 7.48 (t, J=7.7Hz, 1H), 7.41 (t, J=7.7Hz, 1H), 7.36
(d, J=7.5Hz, 2H), 2.49 (s, 3H)
13C NMR(100MHz,CDCl3):δ180.1,152.1,150.1,138.5,134.8,134.8,132.7,
130.9,130.0,129.9,129.4,129.1,127.4,126.3,124.5,124.0,119.6,17.9.
Embodiment 11
Raw material：3- nitro-acetophenones；
Target product：
Yield：88%；
1H NMR(400MHz,CDCl3):δ 9.00 (s, 1H), 8.95 (s, 1H), 8.51 (d, J=8.2Hz, 1H),
8.38 (dd, J=13.2,7.8Hz, 2H), 8.25 (d, J=8.2Hz, 1H), 7.78 (t, J=8.0Hz, 1H),
7.69 (t, J=8.0Hz, 1H), 7.51 (d, J=13.0Hz, 1H), 2.57 (s, 4H)
13C NMR(100MHz,CDCl3):δ178.7,151.0,150.4,148.6,148.2,137.8,134.9,
131.6,130.6,130.0,130.0,127.3,124.4,123.8,123.5,121.4,121.1,17.8.
Embodiment 12
Raw material：4- bromoacetophenones；
Target product：
Yield：80%；
1H NMR(400MHz,CDCl3):δ 7.90 (t, J=8.4Hz, 1H), 7.68 (d, J=7.7Hz, 1H), 7.60 (d, J
=7.9Hz, 1H), 7.34 (s, 1H), 2.48 (s, 1H)
13C NMR(100MHz,CDCl3):δ180.5,152.7,150.2,135.7,132.0,131.8,130.8,
128.2,127.8,123.9,123.4,119.0,18.0.
Embodiment 13
Raw material：4- trifluoromethyl acetophenones；
Target product：
Yield 78%；
(4-(methylthio)-5-(4-(trifluoromethyl)phenyl)furan-2-yl)(4-
(trifluoromethyl)phenyl)methanone
1H NMR(400MHz,CDCl3):δ 8.14 (t, J=9.4Hz, 1H), 7.82 (d, J=7.9Hz, 1H), 7.74 (d, J
=8.0Hz, 1H), 7.39 (s, 1H), 2.52 (s, 1H)
13C NMR(100MHz,CDCl3):δ180.5,151.9,150.4,139.8,134.3,132.4,129.6,
(129.1,128.3,126.6,126.5,125.7 dd, J=7.5,3.7Hz), 125.6 (q, J=3.7Hz), 123.8,120.8,
17.8.
Embodiment 14
Raw material：4- methyl acetophenones；
Target product：
Yield：73%
1H NMR(400MHz,CDCl3):δ 7.99-7.92 (m, 1H), 7.32 (d, J=6.6Hz, 1H), 7.27 (d, J=
8.0Hz,1H),2.45(s,2H),2.40(s,1H).
13C NMR(100MHz,CDCl3):δ181.4,154.12,150.2,143.4,139.2,134.6,129.5,
129.4,129.2,126.8,126.5,124.0,117.2,21.7,21.5,18.1.
Embodiment 15
Raw material：4- chloro-acetophenones；
Target product：
Yield：80%；
1H NMR(400MHz,CDCl3):δ 8.03-7.93 (m, 1H), 7.51 (d, J=8.2Hz, 1H), 7.45 (d, J=
8.3Hz,1H),7.35(s,1H),2.48(s,1H).
13C NMR(100MHz,CDCl3):δ180.3,152.7,150.2,139.2,135.3,135.1,130.7,
129.0,128.9,127.8,127.7,123.9,118.8,18.0.
Embodiment 16
Raw material：4- methoxyacetophenones；
Target product：
Yield：72%；
1H NMR(400MHz,CDCl3):δ 8.05 (dd, J=16.5,7.6Hz, 1H), 7.33 (s, 1H), 7.05-6.94
(m,2H),3.91(s,1H),3.88(s,1H),2.45(s,1H).
13C NMR(100MHz,CDCl3):δ193.5,163.2,160.1,154.0,150.1,132.3,131.7,
129.9,128.1,124.0,122.4,114.3,114.1,113.7,55.5,55.3,18.3.
Embodiment 17
Raw material：4- methylthio phenyl ethyl ketones；
Target product：
Yield 63%；
1H NMR(400MHz,CDCl3):δ 7.98 (d, J=8.2Hz, 1H), 7.33 (t, J=6.4Hz, 1H), 7.26 (s,
1H),2.56(s,1H),2.53(s,1H),2.47(s,1H).
13C NMR(100MHz,CDCl3):δ180.5,153.4,150.2,145.5,140.3,133.3,129.8,
126.7,126.0,125.9,125.0,123.9,117.6,18.1,15.2,14.8.
Embodiment 18
Raw material：4- tert-butyl benzene ethyl ketones；
Target product：
Yield：58%；
1H NMR(400MHz,CDCl3):δ 8.01 (d, J=7.8Hz, 1H), 7.52 (dd, J=14.9,7.6Hz, 1H),
7.36(s,1H),2.47(s,1H),1.38(s,2H),1.36(s,2H).
13C NMR(100MHz,CDCl3):δ181.3,156.3,154.0,152.3,150.4,134.5,129.4,
126.8,126.3,125.6,125.4,124.0,117.3,35.1,34.8,31.2,31.1,18.2.
Claims (8)
- A kind of 1. synthetic method of derivative containing thiomethylfuran, it is characterised in that：The acetophenone compounds of formula 1 and dimethyl are sub- Sulfone, the one pot reaction in the presence of simple substance iodine catalyst and potassium persulfate oxidation agent, obtain the furan derivatives of formula 2；Wherein, R is hydrogen, halogenic substituent, trifluoromethyl, nitro, alkyl, alkoxy or methyl mercapto.
- A kind of 2. synthetic method of derivative containing thiomethylfuran according to claim 1, it is characterised in that：The benzene second Concentration of the ketone compounds in dimethyl sulfoxide (DMSO) is 0.1~1mol/L.
- A kind of 3. synthetic method of derivative containing thiomethylfuran according to claim 2, it is characterised in that：The benzene second Concentration of the ketone compounds in dimethyl sulfoxide (DMSO) is 0.2~0.3mol/L.
- A kind of 4. synthetic method of derivative containing thiomethylfuran according to claim 1, it is characterised in that：The simple substance The mole of iodine is the 20~40% of acetophenone compounds mole.
- A kind of 5. synthetic method of derivative containing thiomethylfuran according to claim 4, it is characterised in that：The simple substance The mole of iodine is the 25~35% of acetophenone compounds mole.
- A kind of 6. synthetic method of derivative containing thiomethylfuran according to claim 1, it is characterised in that：The over cure The mole of sour potassium oxidant is 2~3 times of acetophenone compounds mole.
- 7. a kind of synthetic method of derivative containing thiomethylfuran according to any one of claim 1~6, its feature exist In：The condition of the reaction：Reaction temperature is 90~140 DEG C, and the reaction time is 5~11h.
- A kind of 8. synthetic method of derivative containing thiomethylfuran according to claim 7, it is characterised in that：The reaction Condition：Reaction temperature is 100~130 DEG C, and the reaction time is 6~10h.
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| CN108358877A (en) * | 2018-04-24 | 2018-08-03 | 沅江华龙催化科技有限公司 | A kind of furyl neighbour derovatives and preparation method thereof |
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| CN108358877A (en) * | 2018-04-24 | 2018-08-03 | 沅江华龙催化科技有限公司 | A kind of furyl neighbour derovatives and preparation method thereof |
| CN108503612A (en) * | 2018-04-24 | 2018-09-07 | 沅江华龙催化科技有限公司 | A kind of method of phenylpropyl alcohol ketone class compound and dimethyl sulfoxide (DMSO) structure furane derivative derivative |
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| CN108503612B (en) * | 2018-04-24 | 2019-09-17 | 沅江华龙催化科技有限公司 | A kind of method of phenylpropyl alcohol ketone class compound and dimethyl sulfoxide building furane derivative derivative |
| CN108658906B (en) * | 2018-04-24 | 2019-11-05 | 沅江华龙催化科技有限公司 | A kind of synthetic method of furane derivative radical derivative |
| CN108383803A (en) * | 2018-05-08 | 2018-08-10 | 沅江华龙催化科技有限公司 | A kind of synthetic method of 2,4 2 substituted oxazoline |
| CN108440438A (en) * | 2018-05-08 | 2018-08-24 | 沅江华龙催化科技有限公司 | A method of 2,4 diaryl oxazoles are built jointly by acetophenone compounds and ammonium persulfate and dimethyl sulfoxide (DMSO) |
| CN108440438B (en) * | 2018-05-08 | 2020-04-21 | 沅江华龙催化科技有限公司 | Method for constructing 2, 4-diaryl oxazole by acetophenone compounds, ammonium persulfate and dimethyl sulfoxide |
| CN115340513A (en) * | 2022-09-26 | 2022-11-15 | 济南悟通生物科技有限公司 | Preparation method of 2-methyl-3-methylmercaptofuran |
| CN115340513B (en) * | 2022-09-26 | 2023-03-10 | 济南悟通生物科技有限公司 | Preparation method of 2-methyl-3-methylmercapto furan |
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