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Chemical Structure| 124391-75-9
Chemical Structure| 124391-75-9
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CAS No. :124391-75-9 MDL No. :MFCD17015961
Formula : C5H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :PCPUMGYALMOCHF-YFKPBYRVSA-N
M.W : 102.13 Pubchem ID :40784875
Synonyms :

Safety of [ 124391-75-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 124391-75-9 ]

* 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 [ 124391-75-9 ]
  • Downstream synthetic route of [ 124391-75-9 ]

[ 124391-75-9 ] Synthesis Path-Upstream   1~23

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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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  • [ 865-33-8 ]
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Reference: [1] Organic Letters, 2013, vol. 15, # 19, p. 5072 - 5075
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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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YieldReaction ConditionsOperation in experiment
86% With methanesulfonic acid In toluene for 5 h; Reflux A 500 ml four-necked reaction bottle was charged with 152 g of diethyl malonate (0.3375? Ols) and 27.6 g of isopropanol solution of 20percent sodium isopropoxide prepared by sodium isopropoxide, 152. 2 g, Min, temperature 25 ° C ~ 28 ° C began dropping 2-bromoethanol 46. 5g (0. 3720mol), drop Bi warming to 50 ° C, insulation reaction 1. 5 hours, 75 ° C below the rotary evaporator steam (0.3172 mol), pure 97percent (GC), in 94percent yield, as a colorless oily liquid, 2-hydroxyethyl-malonic acid diethyl ester(2) To a 500 ml four-necked reaction flask, 66.7 g (0.3172 mol) of 2-hydroxyethylmalonic acid diethyl ester was added, and 76.lg of 20percent sodium hydroxide solution was added, the temperature was raised to 45 ° C, Reaction 2 hours, cooling to 25 ° C, adding 20percent hydrochlori3) Into an autoclave, 47.4 g (0.3045 mol) of 2-hydroxyethyl-malonic acid, 50 g of water and 2.3 g of Cu / Si02 were charged, and the reaction vessel was purged with nitrogen for 3-5 times, Pressure, 240 ° C reaction for 4 hours, filter catalyst in colorless or light yellow oil 2-hydroxymethyl-1,4-butanediol 36. 2g (0.2797mol), purity: 96percent (GC) Yield 95percentc acid 69. 5g, adjust P Ρ = 6-7,80 ° C the following decompression evaporated and filtered to give a colorless oily liquid 2-hydroxyethyl malonic acid 47. 4 g (0.3045?: 1) Purity: 95percent (GC), Yield: 96percent. (3) Into an autoclave, 47.4 g (0.3045 mol) of 2-hydroxyethyl-malonic acid, 50 g of water and 2.3 g of Cu / Si02 were charged, and the reaction vessel was purged with nitrogen for 3-5 times, Pressure, 240 ° C reaction for 4 hours, filter catalyst in colorless or light yellow oil 2-hydroxymethyl-1,4-butanediol 36. 2g (0.2797mol), purity: 96percent (GC) Yield 95percent. 4) To a 500 ml reaction flask equipped with a reflux condenser, 36.2 g (0.2797 mol) of 2-hydroxymethyl-1,4-butanediol, 150 g of toluene and 1.6 g of methanesulfonic acid were charged, The reaction was terminated for 5 hours and the solvent was distilled off under reduced pressure to give 25.2 g (0.1918 mol) of 3-tetrahydrofuran methanol as a pale yellow oil in 95percent purity (GC)Yield 86percent
83.1% at 100℃; for 12 h; In 250 ml dry four-necked flask, add 85percent phosphoric acid 220g, 2-hydroxymethyl-1,4-butanediol 120g,Stir and incubate at 100°C and stir the reaction 12 until the material disappears(TLC monitoring: developing agent PE:EA=1:1);After the reaction is complete, slowly pour 280g of K2CO3 dissolved in 280g of water, mix and degassed completely and determine the pH is about neutral, add ethyl acetate 150ml and stir to extract.Separated, the aqueous layer was extracted twice with ethyl acetate, each time 120 ml, and the organic layers were combined and dried under reduced pressure to give 92.2 g of a tan oily liquid;The fractions of 50 to 60°C/500 Pa were collected by distillation under reduced pressure to obtain 84.9 g of a colorless oily liquid in a yield of 83.1percent and a purity of 99percent.
80% With toluene-4-sulfonic acid In toluene at 110℃; for 9 h; The 2-hydroxymethyl-1,4-butanediol prepared in step (2) was purified without addition of a 500 ml three-necked reaction flask equipped with a water separator and a reflux condenser, and toluene 120 Ml as solvent, adding 0.6 g p-toluenesulfonic acid, temperature control 110 reaction 9 hours, HPLC detection to the raw material reaction is complete, you can stop the reaction.The fractions were collected by distillation under reduced pressure at 72 to 76 ° C and 133 to 266 Pa to give 41 g of 3-hydroxymethyltetrahydrofuran in 80percent yield and 99percent purity
Reference: [1] Patent: CN105254598, 2016, A, . Location in patent: Paragraph 0007; 0022
[2] Patent: CN103709126, 2018, B, . Location in patent: Paragraph 0029; 0035; 0036; 0044
[3] Patent: CN104193701, 2016, B, . Location in patent: Paragraph 0023
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YieldReaction ConditionsOperation in experiment
98.7% With 5%-palladium/activated carbon; hydrogen In ethanol at 20℃; for 2 h; Autoclave; Large scale third step,8.87 kg (88.6 mol) of 3-formyltetrahydrofuran was added to the autoclave.5percent Pd/C 0.44kg, and 100L ethanol,After replacing the gas in the kettle three times with nitrogen, the H2 is introduced to a total pressure of 6.5 MPa.The reaction was stirred at room temperature for 2 h, and Pd/C was removed by filtration, and concentrated to remove ethanol.Distillation under reduced pressure gave 8.93 kg (87.4 mol) of 3-hydroxymethyltetrahydrofuran.The yield was 98.7percent.
Reference: [1] Patent: CN108530401, 2018, A, . Location in patent: Paragraph 0033; 0034; 0037; 0043
[2] Patent: EP1354881, 2003, A1, . Location in patent: Page/Page column 6-7
[3] Patent: EP1354881, 2003, A1, . Location in patent: Page/Page column 6-7
[4] Patent: EP1354881, 2003, A1, . Location in patent: Page/Page column 6-7
[5] Patent: EP1354881, 2003, A1, . Location in patent: Page/Page column 6-7
[6] Patent: EP1354881, 2003, A1, . Location in patent: Page/Page column 6-7
[7] Patent: EP1354881, 2003, A1, . Location in patent: Page/Page column 6-7
[8] Patent: EP1354881, 2003, A1, . Location in patent: Page/Page column 6-7
[9] Patent: EP1354881, 2003, A1, . Location in patent: Page/Page column 6-7
[10] Patent: EP1354881, 2003, A1, . Location in patent: Page/Page column 6-7
[11] Patent: EP1354881, 2003, A1, . Location in patent: Page/Page column 6-7
[12] Patent: EP1354881, 2003, A1, . Location in patent: Page/Page column 6-7
[13] Patent: WO2017/156165, 2017, A1, . Location in patent: Paragraph 00595-00597
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YieldReaction ConditionsOperation in experiment
90% With sodium tetrahydroborate In tetrahydrofuran at 60℃; for 8 h; 18.5 g in a 250 mL three-necked round bottom flask a-hydroxymethyl-γ-butyrolactone dissolved in60 mL of tetrahydrofuran,Then 6.0 g of sodium borohydride was added,Control temperature 60 insulation reaction 8h,TLC tracking,a-hydroxymethyl-γ-butyrolactone conversion of 97percent, cooling 10 ° C, add hydrochloric acid, filtration, the filtrate was concentrated,Distillation 16.6 grams of 3-hydroxymethyl tetrahydrofuran,GC method for the determination of content of 93percent, the yield of 90percent.
Reference: [1] Patent: CN106349196, 2017, A, . Location in patent: Paragraph 0049; 0068; 0087
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Reference: [1] Farmaco, Edizione Scientifica, 1984, vol. 39, # 3, p. 171 - 188
[2] Tetrahedron, 1981, vol. 37, p. 781 - 787
[3] ACS Catalysis, 2018, vol. 8, # 2, p. 785 - 789
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Reference: [1] Patent: CN107118183, 2017, A, . Location in patent: Paragraph 0030
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Reference: [1] Patent: CN107698541, 2018, A, . Location in patent: Paragraph 0008
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  • [ 201230-82-2 ]
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Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 38, p. 14306 - 14312
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Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 38, p. 14306 - 14312
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Reference: [1] Synthetic Communications, 2005, vol. 35, # 7, p. 971 - 978
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  • [ 109-99-9 ]
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Reference: [1] Patent: EP1431295, 2004, A1, . Location in patent: Page 4-5
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Reference: [1] Patent: EP1431296, 2004, A1, . Location in patent: Page 5
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YieldReaction ConditionsOperation in experiment
6.9 - 21.5 %Chromat. at 300 - 348℃; for 3 h; A mixture of isopropanol (38.73percent), water (36.74percent), and FTHF (23.81percent) was fed into a one inch tubular reactor filled with Cu/ZrO2 catalyst (130ml catalytic bed) at 37.3-39.4 ml/hr rate at 300-344°C and 800 psi hydrogen pressure. The product was collected every 3 hrs and analyzed by GC. The yield and production rates at full conversion are shown in the Table 3. EXAMPLE 6Reduction of FTHF with Hydrogen, Continuous Run, Repetition of Example 5 Copper / Zirconia Catalyst and secondary alcohol A mixture of isopropanol (21.91percent), water (44.81percent), FTHF (30.86percent) was fed into a one inch tubular reactor filled with Cu/ZrO2 catalyst (130ml catalytic bed) at 37.7-38.8 ml/hr rate at 310-348°C and 800 psi hydrogen pressure. The product was collected every 3hrs and analyzed by GC. The selectivity and production rates are shown in the Table 4. EXAMPLE 7Reduction of FTHF with Hydrogen, Continuous Run, Repetition of Example 5 Copper / Zirconia Catalyst and secondary alcohol A mixture of isopropanol (10.91percent), water (50.88percent), FTHF (35.2percent) was fed into a one inch tubular reactor filled with Cu/ZrO2 catalyst (130ml catalytic bed) at 39.4 ml/hr rate at 310-320°C and 800 psi hydrogen pressure. The product was collected after 3hrs run and analyzed by GC. The selectivity and production rates are shown in the Table 5.
Reference: [1] Patent: EP1431296, 2004, A1, . Location in patent: Page 9-14
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Reference: [1] Synthetic Communications, 2005, vol. 35, # 7, p. 971 - 978
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Reference: [1] Patent: CN105254598, 2016, A,
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Reference: [1] Patent: CN103709126, 2018, B,
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Reference: [1] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 5, p. 1498 - 1503
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Reference: [1] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 5, p. 1498 - 1503
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  • [ 165253-29-2 ]
Reference: [1] Patent: US5614527, 1997, A,
[2] Patent: US2013/252937, 2013, A1,
[3] Patent: WO2013/144097, 2013, A1,
[4] Patent: WO2013/144098, 2013, A1,
[5] Patent: WO2008/101867, 2008, A1,
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Reference: [1] Patent: US6610707, 2003, B1,
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Reference: [1] Patent: WO2012/133861, 2012, A1,
[2] Patent: WO2013/47904, 2013, A1,
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