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[ CAS No. 57595-23-0 ]

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Chemical Structure| 57595-23-0
Chemical Structure| 57595-23-0
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CAS No. :57595-23-0 MDL No. :MFCD19707049
Formula : C6H8O4 Boiling Point : 220°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :144.13 g/mol Pubchem ID :14666564
Synonyms :

Safety of [ 57595-23-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 57595-23-0 ]

  • Upstream synthesis route of [ 57595-23-0 ]
  • Downstream synthetic route of [ 57595-23-0 ]

[ 57595-23-0 ] Synthesis Path-Upstream   1~6

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Reference: [1] Patent: US5294612, 1994, A,
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YieldReaction ConditionsOperation in experiment
24%
Stage #1: With sodium hydride In diethyl ether at 20℃; for 0.5 h;
Stage #2: at 0℃; for 1 h;
To a stirred slurry of sodium hydride (2.2 g, 55 mmol) in dry ether (40 mL) at room temperature (rt) was added methyl glycolate (4.5 g, 50 mmol) dropwise. The reaction mixture was stirred for 14 h, then it was concentrated under vacuo. To the solid was added methyl acrylate (5.2 g, 55 mmol) in DMSO (20 mL) at O0C and the mixture was stirred for 15 min, and the cool bath was removed and it was stirred for 45 min. The mixture was poured into 5percent H2SO4 (60 mL), and it was extracted with ether (150 mL). The organic layer was dried, concentrated and purified by column chromatography to give 1.7 g (24percent) of the title compound. 1H NMR (CDCl3): 4.51-4.40 (m, 2H), 4.03 (q, J = 8.1 Hz, 2H), 3.80 (s, 3H), 3.54 (t, J = 8.1 Hz, IH).
31% With sodium In dimethyl sulfoxide Synthesis of 2,5-dihydro furan 3,4-dicarboxylic acid
2.3 g (0.1 mol) sodium was pulverized under toluene and the solvent was replaced with 75 ml ether. 11 ml (0.1 mol) methylglycolate was added to the mixture under stirring until the evolution of hydrogen gas had ceased.
To the dry sodium derivative remaining after destination of the ether, a solution of 10 ml (0.12 mol) distilled methylacrylate in 50 ml DMSO was added while the reaction was kept at 4° C.
After 15 minutes the solution was stirred for an additional 30-40 min at room temperature and poured into aqueous H2SO4 at 4° C. and extracted with ether.
Washing of the organic layer with a saturated NaCl solution, drying over NaSO4 and removal of the ether was followed by destination under reduced pressure to give 4.5 g (31percent) of 4-oxo-tetrahydro furane 3-carboxylic acidmethyl ester.
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 5, p. 2124 - 2130
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 3, p. 1124 - 1130
[3] Patent: WO2008/21456, 2008, A2, . Location in patent: Page/Page column 32
[4] Patent: WO2018/137573, 2018, A1, . Location in patent: Page/Page column 104
[5] Tetrahedron Letters, 1989, vol. 30, # 45, p. 6129 - 6132
[6] Tetrahedron, 1991, vol. 47, # 27, p. 4847 - 4860
[7] Patent: US2003/203951, 2003, A1,
[8] Patent: WO2016/49100, 2016, A1, . Location in patent: Page/Page column 22; 23
[9] Patent: WO2016/45126, 2016, A1, . Location in patent: Page/Page column 20
[10] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 12, p. 1193 - 1198
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YieldReaction ConditionsOperation in experiment
54%
Stage #1: With sodium hydride In diethyl ether
Stage #2: at 0 - 20℃;
Stage #3: With hydrogenchloride In water; dimethyl sulfoxide
To a suspension of NaH (6.66g, 166.5 mmol) in ether (500 mL) add methyl glycolate (15.0 g, 166.5 mmol) drop wise. Stir the reaction until evolution of H2 gas ceases. Concentrate and dissolve the solid in DMSO (300 mL). Cool the reaction to 0 oC and add methyl acrylate (16.6 mL, 183.17 mmol) drop wise. Warm the reaction to room temperature and stir overnight. Acidify the reaction with 10percent HCl and extract with ether (3X). Combine organic extracts and wash with brine. Dry the organic solution (NA2SO4), filter, and concentrate in vacuo. Purify by flash chromatography (250 g SI02, 40 ML/MIN, 0-50percent ethyl acetate/hexane for 20 minutes and then 50percent ethyl acetate/hexane for 13 minutes) to yield 4-oxo-tetrahydro-furan-3-carboxylic acid methyl ester 4a (12.9g, 89.2 mmol, 54percent) as a colorless OIL. 1H NMR (8, 400 MHz, CDCL3) : 4.50 (dd, 1H, J=8.4, 9.6 Hz), 4.46 (dd, 1H, J=8.4, 9.6 Hz), 4. 05 (d, 1H, J=16.8 Hz), 3.79, (s, 3H), 3.97 (d, 1H, J=16.8, Hz), 3.54 (t, 1H, J=8.4Hz). MS calcd. 144; found (EI) 144.
Reference: [1] Patent: WO2004/94400, 2004, A2, . Location in patent: Page 40
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YieldReaction ConditionsOperation in experiment
26%
Stage #1: With sodium hydride In diethyl ether at 20℃; for 2 h;
Stage #2: at 0 - 20℃; for 1.25 h;
Sodium hydride (4 g, 60percent w/w in oil dispersion, 100 mmol) was added to a flame-dried flask along with ether (100 mL). To the reaction flask under nitrogen atmosphere, methyl glycolate (7.7 mL, 100 mmol) was added slowly with constant stirring. The reaction mixture was allowed to stir at room temperature for 2 hours under nitrogen atmosphere then solvent was removed in vacuo. To the residue, methyl acrylate (10.8 mL, 120 mmol) in DMSO (50 mL) was added in one portion while the reaction flask was kept immersed in an ice bath. The reaction mixture was allowed to stir at 0 °C for 15 minutes then at room temperature for 1 hour. The reaction mixture was then filtered through Celte'3', poured into ice-cold aqueous sulfuric acid solution (150 mL, 2N), and extracted with ether (2 x 200 mL). The organic layer was washed with saturated NaCl solution (500 mL), dried over anhydrous Na2S04, filtered, and solvent was removed in vacuo. The intermediate ketoester was recovered in 26percent yield (3.7 g, 25.7 mmol) afterpurificationby column chromatography on silica using 25percent ethyl acetate/hexanes as the eluent (Rf= 0.3). The ketoester intermediate (3.7g, 25.7 mmol) was added slowly to a solution of sodium hydride (1.4 g, 60percent w/w in oil dispersion, 34 mmol) in ether (80 mL) at 0 °C with constant stirring under nitrogen atmosphere. After 30 minutes, trifluoromethanesulfonic anhydride (5.3 mL, 31.4 mmol) was added dropwise over 5 minutes. The reaction mixture was allowed to stir at 0 °C for an additional 1.5 hours then the reaction was poured into water (80 mL) and the layers were separated. The aqueous phase was washed with dichloromethane (2 x 60 mL) and the organic phases were combined. The organic layer was dried over anhydrous Na2SO4, filtered, and solvent was removed in vacuo. The 2,5- dihydrofuran ester 13a was recovered in 23percent yield (1.6 g, 5.8 mmol) after purification by column chromatography on silica using 25percent ethyl acetate/hexanes as the eluent (Rf= 0.45). MS: calc. for C7H7F306S : 257.9 ; Found: GC-MS 7nl5 275 (MH).
Reference: [1] Patent: WO2005/40109, 2005, A1, . Location in patent: Page/Page column 78-79
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Reference: [1] Patent: US2006/9451, 2006, A1, . Location in patent: Page/Page column 19
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YieldReaction ConditionsOperation in experiment
54% With sodium methylate In ethanol (e)
1-(3-Tetrahydrofuranyl)-3-methyl-5-amino-1H-pyrazole-4-carbonitrile
A mixture of 3-tetrahydrofuranylhydrazine hydrochloride (6.2 g, 0.045 mol), sodium methoxide (2.4 g, 0.045 mol) and ethanol (70 ml) was refluxed under argon for 10 minutes.
The reaction mixture was cooled to room temperature and 1-ethoxyethylidene malononitrile (6.1 g, 0.045 mol) was added.
The reaction mixture was heated to reflux and stirred for 21 hours.
The reaction was cooled and the solvent was removed in vacuo.
The residue was recrystallized from water to afford 4.7 g (54percent) of 1-(3-tetrahydrofuranyl)-3-methyl-5-amino-1H-pyrazole-4-carbonitrile as yellow crystals, m.p. 134°-135° C. when dried at 90° C. in high vacuum.
Reference: [1] Patent: US5294612, 1994, A,
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