Alternatived Products of [ 3795-79-7 ]
Product Details of [ 3795-79-7 ]
CAS No. : | 3795-79-7 |
MDL No. : | MFCD01313010 |
Formula : |
C9H10O2S
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Boiling Point : |
- |
Linear Structure Formula : | - |
InChI Key : | - |
M.W : |
182.24
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Pubchem ID : | - |
Synonyms : |
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Safety of [ 3795-79-7 ]
Signal Word: | Warning |
Class: | |
Precautionary Statements: | P280-P305+P351+P338 |
UN#: | |
Hazard Statements: | H302 |
Packing Group: | |
GHS Pictogram: |
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Application In Synthesis of [ 3795-79-7 ]
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
- Upstream synthesis route of [ 3795-79-7 ]
- Downstream synthetic route of [ 3795-79-7 ]
- 1
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[ 3795-79-7 ]
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[ 22821-70-1 ]
- 2
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[ 3795-79-7 ]
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[ 3446-90-0 ]
Yield | Reaction Conditions | Operation in experiment |
96% |
With hydrogen; C28H25BrMnN2O2P; lithium tert-butoxide In propan-1-ol at 100℃; for 5h; Autoclave; |
|
85% |
With HN(CH2CH2C3H3N2Mes)2Cl2; potassium <i>tert</i>-butylate; hydrogen; cobalt(II) chloride In tetrahydrofuran at 100℃; for 16h; Autoclave; Glovebox; |
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With lithium aluminium tetrahydride |
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Reference:
[1]Li, Xiao-Gen; Li, Fu; Xu, Yue; Xiao, Li-Jun; Xie, Jian-Hua; Zhou, Qi-Lin
[Advanced Synthesis and Catalysis, 2022, vol. 364, # 4, p. 744 - 749]
[2]Shao, Zhihui; Zhong, Rui; Ferraccioli, Raffaella; Li, Yibiao; Liu, Qiang
[Chinese Journal of Chemistry, 2019, vol. 37, # 11, p. 1125 - 1130]
[3]Grice,R.; Owen,L.N.
[Journal of the Chemical Society, 1963, p. 1947 - 1954]
- 3
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[ 201230-82-2 ]
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[ 104-95-0 ]
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[ 13205-48-6 ]
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[ 3795-79-7 ]
Yield | Reaction Conditions | Operation in experiment |
1: 70.5%
2: 11.5% |
With methanol; tert-Amyl alcohol; sodium hydride In tetrahydrofuran at 40℃; for 71h; Irradiation; |
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- 4
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[ 67-56-1 ]
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[ 3446-90-0 ]
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[ 3795-79-7 ]
Yield | Reaction Conditions | Operation in experiment |
94% |
With Rh(trop2N)(PPh3); methacrylic acid methyl ester In tetrahydrofuran at -30 - 25℃; for 4h; chemoselective reaction; |
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85% |
With palladium 10% on activated carbon; oxygen; sodium carbonate at 120℃; for 1.5h; Microwave irradiation; Green chemistry; |
General procedure for aerobic aldehyde and alcohol esterification
General procedure: Na2CO3 (2 equiv) was dissolved in MeOH (1 mL) and sonicated with a US bath for 10 sec (20.3 kHz, 60 W). The substrate (aldehyde or alcohol, 1 mmol) and 10% Pd/C (5% Pd/mol of substrate) were added to this mixture. The reaction was carried out under magnetic stirring in a MW reactor Synth-Wave. The 1 L pressure-resistant PTFE cavity (up to 200 bar) equipped with a 15 position vial rack was loaded with O2 (2.5 bar) followed by the addition of N2 up to 20 bar total pressure. The reaction was irradiated for an appropriate reaction temperature ranging from 90 to 120 °C (average power 300 W), and for 1 to 2 hours (see Table 2 and Table 3). The mixture was then filtered off through celite, the catalyst washed with MeOH and the solvent evaporated under vacuum. Isolated yields for all substrates reported were obtained using these conditions. |
72% |
With bismuth(lll) trifluoromethanesulfonate; dichloro bis(acetonitrile) palladium(II); oxygen; potassium carbonate at 60℃; for 3h; Schlenk technique; |
3.15 4.2.1 General procedure for the synthesis of 2 in Table2
General procedure: To a 25-mL Schlenk tube equipped with a magnetic stirrer, PdCl2(CH3CN)2 (0.05mol, 5mol%), Bi(OTf)3 (0.05mol, 5mol%), K2CO3 (1mmol) were added. Substrates 1 (1mmol) and MeOH (2mL) were added subsequently. The reaction tube was vacuumed and backfilled with oxygen (3 times). Then the reaction mixture was stirred at 60°C for 3h in the presence of an oxygen balloon. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. Subsequently, the combined organic layer was concentrated under reduced pressure and the crude product was purified by column chromatography with hexane/ethyl acetate to afford the corresponding products 2. |
94 %Chromat. |
With oxygen; potassium carbonate at 60℃; for 24h; Schlenk technique; Green chemistry; |
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92 %Chromat. |
With potassium carbonate at 55℃; for 24h; |
S6. Procedure for the synthesis of esters
General procedure: A magnetic stir bar and the alcohol substrate were transferred to 20 mL glass tube and then 2 mL of MeOH oralcohol was added. Then, 35 mg catalyst and 10 mol% of K2CO3 were added. The glass tube containingreaction mixture was fitted with septum and connected to a balloon containing one bar air. Then the glass tubewas placed into a preheated aluminum block at 60°C. Temperature inside the reaction tube was measured tobe 55 oC and this temperature has been taken as the reaction temperature. After completion of the reaction,the glass tube was cooled down to room temperature. Af terwards, the catalyst was f iltered-off and washedwith methanol. The solvent from the filtrate containing the reaction products was removed in vacuum and thecorresponding ester was purified by column chromatography. Products were analyzed by GC-MS and NMRspectroscopy analysis. In the case of yields determined the by GC, 100 μL n-hexadecane was added to thereaction vial containing the products and diluted with ethyl acetate. Then catalyst was f iltered through a plugof silica and the filtrate containing product was analyzed by GC. |
Reference:
[1]Zweifel, Theo; Naubron, Jean-Valere; Gruetzmacher, Hansjoerg
[Angewandte Chemie - International Edition, 2009, vol. 48, # 3, p. 559 - 563]
[2]Caporaso, Marina; Cravotto, Giancarlo; Georgakopoulos, Spyros; Heropoulos, George; Martina, Katia; Tagliapietra, Silvia
[Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 1454 - 1461]
[3]Hu, Yongke; Li, Bindong
[Tetrahedron, 2017, vol. 73, # 52, p. 7301 - 7307]
[4]Jagadeesh, Rajenahally V.; Junge, Henrik; Pohl, Marga-Martina; Radnik, Joerg; Brueckner, Angelika; Beller, Matthias
[Journal of the American Chemical Society, 2013, vol. 135, # 29, p. 10776 - 10782]
[5]Bartling, Stephan; Beller, Matthias; Chandrashekhar, Vishwas G.; Jagadeesh, Rajenahally V.; Rabeah, Jabor; Rockstroh, Nils; Senthamarai, Thirusangumurugan
[Chem, 2022, vol. 8, # 2, p. 508 - 531]
- 5
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[ 67-56-1 ]
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[ 201230-82-2 ]
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[ 190788-58-0 ]
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[ 3795-79-7 ]
- 6
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[ 3446-90-0 ]
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[ 865-33-8 ]
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[ 3795-79-7 ]
Yield | Reaction Conditions | Operation in experiment |
82% |
With tellurium; bismuth (III) nitrate pentahydrate; 5%-palladium/activated carbon; oxygen In methanol at 60℃; for 8h; |
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- 7
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[ 1126-46-1 ]
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[ 616-38-6 ]
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[ 3795-79-7 ]
Yield | Reaction Conditions | Operation in experiment |
71% |
With potassium <i>tert</i>-butylate; palladium diacetate; triphenylphosphine; potassium thioacetate In dimethyl sulfoxide at 120℃; Inert atmosphere; |
14 Example 14
Under a nitrogen atmosphere,The substrate p-chlorobenzoic acid methyl ester 1e was added to a 25 mL test tube reactor(0.2mmol,72.2mg),KSAc(0.6mmol,68.4mg),DMC(1.0mmol,90mg),Pd(OAc)2(0.01mmol,2.3mg),PPh3(0.02mmol,5.9mg),tBuOK(0.6mmol,69.2mg),and DMSO(2.0mL).The reaction was heated to 120 ° C to carry out the reaction.After the TLC detection reaction was completed,The system was cooled to room temperature.The reaction was quenched with saturated aqueous ammonium chloride,And extracted with ethyl acetate (3 * 10 mL)The product was purified by column chromatography to give 25.8 mg (71%) of product 2e. |
71% |
With potassium <i>tert</i>-butylate; palladium diacetate; triphenylphosphine; potassium thioacetate In dimethyl sulfoxide at 120℃; Schlenk technique; Inert atmosphere; |
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Reference:
[1]Current Patent Assignee: EAST CHINA NORMAL UNIVERSITY - CN106866327, 2017, A
Location in patent: Paragraph 0080; 0081; 0082
[2]Wang, Ming; Qiao, Zongjun; Zhao, Jiaoyan; Jiang, Xuefeng
[Organic Letters, 2018, vol. 20, # 19, p. 6193 - 6197]