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[ CAS No. 89364-31-8 ]

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Chemical Structure| 89364-31-8
Chemical Structure| 89364-31-8
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CAS No. :89364-31-8 MDL No. :MFCD00075173
Formula : C5H8O3 Boiling Point : 140°C at 760 mmHg
Linear Structure Formula :- InChI Key :N/A
M.W :116.12 g/mol Pubchem ID :4661317
Synonyms :

Safety of [ 89364-31-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338+P310-P312-P332+P313-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H303-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 89364-31-8 ]

  • Upstream synthesis route of [ 89364-31-8 ]
  • Downstream synthetic route of [ 89364-31-8 ]

[ 89364-31-8 ] Synthesis Path-Upstream   1~11

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Reference: [1] Helvetica Chimica Acta, 2003, vol. 86, # 5, p. 1371 - 1396
[2] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 18, p. 4093 - 4102
[3] Yakugaku Zasshi, 1957, vol. 77, p. 232,234[4] Chem.Abstr., 1957, p. 11344
[5] Tetrahedron, 1981, vol. 37, p. 781 - 787
[6] Farmaco, Edizione Scientifica, 1984, vol. 39, # 3, p. 171 - 188
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  • [ 124391-75-9 ]
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Reference: [1] ACS Catalysis, 2018, vol. 8, # 7, p. 6738 - 6744
[2] Bulletin of the Chemical Society of Japan, 2009, vol. 82, # 8, p. 1000 - 1002
[3] Synthetic Communications, 1999, vol. 29, # 17, p. 2937 - 2942
[4] Organic Process Research and Development, 2017, vol. 21, # 9, p. 1388 - 1393
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  • [ 79710-86-4 ]
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Reference: [1] Patent: US6881851, 2005, B1, . Location in patent: Page/Page column 3-5
[2] Advanced Synthesis and Catalysis, 2010, vol. 352, # 2-3, p. 463 - 477
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  • [ 130193-90-7 ]
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Reference: [1] Patent: WO2013/93850, 2013, A1, . Location in patent: Page/Page column 100; 101
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Reference: [1] Journal of the American Chemical Society, 1958, vol. 80, p. 3905,3907
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Reference: [1] Patent: WO2013/93850, 2013, A1,
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  • [ 53662-85-4 ]
YieldReaction ConditionsOperation in experiment
67% for 18 h; Reflux To a solution of tetrahydro-3-furancarboxylic acid (20.00 g, 172 mmol) in MeOH (350 mL) was added sulfuric acid (27.54 mL, 517 mmol).
The reaction was heated to reflux for 18 h.
The reaction was then cooled to rt and concentrated.
The residue was partitioned between water (500 mL) and DCM (200 mL).
The phases were separated and the aqueous fraction was extracted with DCM (200 mL).
The combined organic fractions were washed with saturated aqueous NaHCO3 (200 mL) and brine (200 mL), dried over Na2SO4, filtered, and concentrated to afford methyl tetrahydro-3-furancarboxylate (15.0 g, 67percent yield) as a pale yellow oil. 1H NMR (400 MHz, DMSO-d) δ ppm 3.85 (t, J=8.4 Hz, 1H), 3.77-3.66 (m, 3H), 3.62 (s, 3H), 3.07-3.22 (m, 1H), 1.97-2.12 (m, 2H).
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 8, p. 2690 - 2694
[2] Patent: US2018/201610, 2018, A1, . Location in patent: Paragraph 0076; 0077
[3] Advanced Synthesis and Catalysis, 2010, vol. 352, # 2-3, p. 463 - 477
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Reference: [1] Patent: WO2014/111496, 2014, A1, . Location in patent: Page/Page column 172; 173
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YieldReaction ConditionsOperation in experiment
2.27 g
Stage #1: With triethylamine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 1 h;
Stage #2: With hydrazine In tetrahydrofuran at 20℃; for 1 h;
(S)-Tetrahydrofuran-3-carbohydrazide and (R)-tetrahydrofuran-3-carbohydrazide, Example 6.1 (1014) To a mixture of tetrahydro-3-furanoic acid (2.0 mL, 20.9 mmol) and TEA (5.8 mL, 42 mmol) in THF (42 mL) was added dropwise isobutyl chloroformate (2.86 mL, 23.00 mmol). The resulting mixture was stirred at 0° C. for 1 h before hydrazine (0.67 mL, 23.00 mmol) was added. The resulting mixture was allowed to stir at RT for 1 h. The mixture was then concentrated, and chloroform (200 mL) and water (20 mL) were added to dissolve the residue. The organic layer was separated, and the aqueous phase was lyophilized. EtOH (50 mL×3) was used to triturate the solid 3 times. The combined EtOH solution was concentrated and dried to give tetrahydrofuran-3-carbohydrazide (2.27 g). LCMS ESI (pos) m/z=131.1 (M+H)+.
Reference: [1] Patent: US2017/320860, 2017, A1, . Location in patent: Paragraph 1013; 1014
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Reference: [1] Patent: US2013/165436, 2013, A1,
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YieldReaction ConditionsOperation in experiment
85% With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 3 h; To a solution of tetrahydrofuran-3-carboxylic acid (0.247 mL, 2.58 mmol) in THF (13 mL) at 0 °C was added slowly lithium aluminium hydride (1 .0 M in THF, 5.2 mL, 5.16 mmol), stirred for 10 minutes then allowed to attain room temperature and stirred for a further 3 hours. The reaction mixture was cooled to 0 °C and diluted with diethyl ether (15 mL), then treated sequentially with water (0.2 mL), NaOH (15percent solution, 0.2 mL) and water (0.6 mL) and stirred for 30 minutes. The white suspension was then treated with sodium sulfate, stirred for a further 20 minutes, filtered over celite, washed with diethyl ether (2x 20 mL) and concentrated in vacuo to yield 224 mg (85percent) of the title compound as a colourless oil which was carried forward to the next stage without further purification. -NMR Spectrum: δΗ (500 MHz, CDCI3): 3.90-3.84 (2H, m), 3.78-3.73 (1H, m), 3.66-3.63 (2H, m), 3.61-3.57 (1H, m), 2.51-2.46 (1H, m), 2.08-2.01 (1H, m), 1.69-1.62 (1H, m)
38%
Stage #1: With borane-THF In tetrahydrofuran at 0 - 65℃; for 12 h;
Stage #2: at 65℃; for 2 h;
Step 1 : To a solution of tetrahydrofuran-3-carboxylic acid (600 mg, 5.17 mmol) in THF (15 mL) was added a solution of 1 M BH3 THF in THF (10.3 mL, 10.3 mmol) at 0 °C. The reaction was heated to 65 °C and stirred for 12 hours. The solution was then cooled to 20 °C and MeOH (4 mL) was added. The reaction was then stirred at 65 °C for 2 hours before cooling to RT and concentrated in vacuo. The residue was purified by flash chromatography on silica gel using a gradient of ethyl acetate and petroleum ether to give (tetrahydrofuran-3-yl)methanol 200 mg (38percent)
>99.9 %Chromat. at 199.84℃; for 10 h; Autoclave General procedure: The hydrogenation of carboxylic acids or other substrates was performed in a high-pressure stainless-steel autoclave (Xinyuan Chemical Machinery, Series CJK, 300 mL) with a maximum stirring rate of 1500 r/min. In a typical experiment, 0.2 g of catalyst (or without catalyst for the control experiment), 3 mmol of the substrate, and 100 mL alkane solvent (n-hexane, n-heptane, i-octane, or n-dodecane) were well mixed in the autoclave and purged with pure nitrogen at room temperature. The gas supply and discharge were carried out manually through needle valves. The autoclave was rapidly heated to the desired temperature and hydrogen was introduced at 2 MPa to initiate the reaction. The reaction pressure was kept at 2 MPa with a small negative deviation (∼0.2 MPa) owing to the consumption of hydrogen. Samples of the liquid phase were continuously taken through a sampling tube with a filter at certain intervals. The stirring rate was kept at 750 r/min during the reaction.
Reference: [1] Patent: WO2017/55860, 2017, A1, . Location in patent: Page/Page column 211; 212
[2] Patent: WO2016/55618, 2016, A1, . Location in patent: Page/Page column 43
[3] Tetrahedron, 1981, vol. 37, p. 781 - 787
[4] Farmaco, Edizione Scientifica, 1984, vol. 39, # 3, p. 171 - 188
[5] Chinese Journal of Catalysis, 2018, vol. 39, # 2, p. 250 - 257
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