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CAS No. : | 36878-91-8 | MDL No. : | MFCD00011566 |
Formula : | C9H10O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OVPIQFGJQAQWAJ-UHFFFAOYSA-N |
M.W : | 182.17 | Pubchem ID : | 336409 |
Synonyms : |
|
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In ethanol; at 25℃; for 12h;Heating / reflux; | 4-Hydrazine benzoic acid (2.18 g, 10 mmol) and ethyl 3-furan-3-yl-3-oxo-propionate (1.58 mL, 10 mmol) were dissolved in ethanol (30 mL), stirred at 25C for 2 hours, and then refluxed for 10 hours. Next, ethanol was distilled off, and solids precipitated from the obtained residue using hexane / ethyl acetate / tetrahydrofuran were collected by filtration. A pale yellow solid (2.37 g, 90% yield) was obtained |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Step 1 4-(3-Furyl)-7-methoxy-2-quinolinone Following the procedures described in Example 1, Steps 1 and 2, but substituting ethyl beta-oxo-3-furanpropionate for ethyl benzoylacetate, the title compound was obtained as a beige solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; In 1,4-dioxane; ethanol; | 3-(3-furyl)-1-(4-nitrophenyl)-1H-pyrazol-5-ol Ethyl beta-oxo-3-furanpropionate (2 g, 10.9 mmol) in ethanol (100 mL) was added p-nitrophenylhydrazine (1.77 g, 11.6 mmol) and 4M HCl in dioxane. The mixture was heated to reflux for 3 hours. Upon cooling to room temperatur, the solvent was removed and the crude product was used in the next step without further purification. MS (APCI) m/e 270 (M-H)-; 1H NMR (DMSO-d6, 300 MHz) delta8.35 (d, 2H), 8.20 (s, 1H), 8.13 (d, 2H), 7.75 (t, 1H), 6.88 (d, 1H), 6.90 (s, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With trifluoromethanesulfonic acid anhydride; triethylamine; In hexane; dichloromethane; ethyl acetate; | Part A. Ethyl (Z)-3-(2-furyl)-3-[(trifluoromethyl)sulfonyl]-oxy}-2-propenoate To a solution of ethyl B-oxo-3-furanpropionate (1 g, 5.49 mmol) in 5 ml anhydrous dichloromethane was added triethylamine (0.847 ml, 6.04 mmol). Reaction was cooled under argon to -78 C. to which trifluoromethanesulfonic anhydride (1.02 ml, 6.04 mmol) was added dropwise via syringe over 5 minutes. Reaction was allowed to warm to room temperature and stirred over night. Next morning the reaction was diluted with 25 ml dichloromethane, organic was washed with 2*50 ml water, 2*50 ml 1N HCl, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude oil was chromatographed on silica gel using 20% EtOAc in hexane as the eluent to give ethyl (Z)-3-(2-furyl)-3-[(trifluoromethyl)sulfonyl]-oxy}-2-propenoate (1.6 g, 93%) as a light brown solid after drying. H1NMR (CDCl3) 1.31-1.35 (t, 3H); 4.26-4.314 (m, 2H); 6.065 (s, H); 6.522 (s, H); 7.47 (s, H); 7.76 (s, H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | 4-[2-[3-(1 -methylethyl)-1 H-pyrazol-4-yl]methyl}tetrahydro-1 (2H)-pyridazinyl]-1 - naphthalenecarbonitrile (C179) EPO <DP n="124"/>To a 250-ml round bottom flask equipped with a magnetic stir bar and nitrogen inlet was added ethyl 3-(3-furanyl)-3-oxopropanoate (1g, 5. deltammoles) followed by [bis(methyloxy)methyl]dimethylamine (10ml). The reaction was allowed to stir at room temperature overnight. The volatiles were removed in vacuo. The crude product (5.5 mmoles) was used without characterization or purification. To this crude product was added acetic acid (10ml) and hydrazine hydrate (0.83g, 3eq) and heated at 100 0C overnight. After cooling to room temperature, the volatiles were removed under reduced pressure. The residue was partitioned between ethyl acetate and 0.1 N NaOH (pH ~10). The phases were separated and the organic fraction was washed twice with water, once with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to yield quantitative yield of crude pyrazole ester. This crude product was used without purification. The pyrazole ester (5.5 mmoles) in diethyl ether ( 5ml) was added dropwise to a precooled (0 0C) suspension of lithium aluminumhydride (330mg, 1.5eq) in diethyl ether (10ml). The reaction mixture was allowed to stir for 1hr at room temperature at which point 0.4ml of water was added very slowly, 0.4ml of 5N NaOH, and 1.2ml of water. This mixture was allowed to stir for 2hrs resulting in the precipitation of a white solid. The reaction mixture was filtered through Celite and the salts were washed with copious amounts of ethyl acetate and methanol. The filtrate was concentrated to yield 540mg (60% yield) of crude pyrazole alcohol. To the crude pyrazole alcohol was added acetone (10ml) followed by manganese dioxide (2.9g,10eq) and the reaction was stirred at 500C for 4hrs. After cooling to room temperature the reaction was filtered through Celite and washed with acetone. The filtrate was concentrated to yield 300mg (56% yield) of the pyrazole aldehyde. The above aldehyde (100mg, 2eq) was coupled with B1 (75mg, 1eq) via the reductive amination procedure outlined in Example 1 (C1) to yield 45mg of the title compound. MS(m/z) ESI ES+ = 384 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With PPA; In tetrahydrofuran; hexane; ethyl acetate; | Step 1: 4-(3-Furyl)-7-hydroxycoumarin A mixture of ethyl 3-oxo-3-(3-furyl)propionate (Aldrich; 3.17 g) and resorcinol (3.83 g) was treated with polyphosphoric acid (15 g) and heated to 110 C. under nitrogen. After 2 hr., the tarry mixture was cooled, then H2 O and THF were added until a solution was obtained. Brine and EtOAc were added, the organic layer was removed and washed twice with brine. Chromatography of the residue, after concentration, using hexane/EtOAc 2:1 followed by swishing the product with ether afforded the title compound as a solid, m.p. 229-232 C. | |
With PPA; In tetrahydrofuran; hexane; ethyl acetate; | Step 1: 4-(3-Furyl)-7-hydroxycoumarin A mixture of ethyl 3-oxo-3-(3-furyl)propionate (Aldrich; 3.17 g) and resorcinol (3.83 g) was treated with polyphosphoric acid (15 g) and heated to 110 C. under nitrogen. After 2 hr, the tarry mixture was cooled, then H2 O and THF were added until a solution was obtained. Brine and EtOAc were added, the organic layer was removed and washed twice with brine. Chromatography of the residue, after concentration, using hexane/EtOAc 2:1 followed by swishing the product with ether afforded the title compound as a solid, m.p. 229-232 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In 5,5-dimethyl-1,3-cyclohexadiene; water; | Step 1 4-(3-Furyl)-7-methoxy-2-quinolinone A solution of m-anisidine (6.2 mL), ethyl beta-oxo-3-furan-propionate (8.4 g) and pyridine (10 drops) in xylene (15 mL) was heated at reflux for 15 hr. The mixture was cooled to r.t. and concentrated. The residual material was subjected to chromatography (silica gel; hexane/EtOAc (2:1)), affording the beta-keto amide as an oil. A portion of this material (2.5 g), O-phosphoric acid (30 mL of 85% acid), and water (30 mL) was heated at 100-110 C. for 5 hr. After cooling to room temperature, H2 O (100 mL) was added and the precipitate that formed was collected by filtration. The title compound was obtained as a mixture with the regioisomeric product, 4-(3-furyl)-5-methoxy-2-quinolinone. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; In 1,4-dioxane; water; isopropyl alcohol; | Method B: A mixture of 894 mg of ethyl 3-(furan-3-yl)-3-oxopropionate (4.90 mmol) and 347 mg of 3-hydroxypropionitrile (4.88 mmol) was heated in an oil bath to 180-205 C. for 0.5 hrs. The reaction mixture was cooled and distilled under reduced pressure. Three fractions were obtained. 1 H NMR indicated that the third fraction (bp 100-140 C. (0.5 mm Hg)) was a 1:1 mixture of ethyl 3-(furan-3-yl)-3-oxopropionate and 2-cyanoethyl 3-(furan-3-yl)-3-oxopropionate. This mixture was used in the condensation step after spectral characterization. A solution of the 3-oxoesters (approximately 1.67 mmol), 192 mg of methyl 3-aminocrotonate (1.67 mmol), and 252 mg of 4-nitrobenzaldehyde (1.67 mmol) in 5 mL of isopropanol was heated at reflux temperature for 30 hrs, cooled, and the solvent was removed in vacuo. The residue was dissolved in 15 mL of dioxane and 15 mL of water (containing 35 mg of NaOH), stirred for 0.5 hr, and concentrated in vacuo. The residue was partitioned between ethyl acetate and water (20 mL each), separated, and the aqueous extract was washed with ethyl acetate (2*20 mL). The organic solutions were discarded. The aqueous extract was acidified with concentrated HCl (pH=3), and the resulting cloudy mixture was extracted with ethyl acetate (2*30 mL). The combined organic extracts were dried (Na2 SO4), and the solvent was removed in vacuo to give 2-(furan-3-yl)-1,4-dihydro-5-methoxycarbonyl-6-methyl-4-(4-nitro)phenylpyridine-3-carboxylic acid as a yellow oil that partially solidified under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With piperidine; acetic acid; In ethanol; for 5h;Reflux; | General procedure: Catalytic amounts of piperidine and acetic acid were added to a mixture of 2-hydroxy-1-naphthaldehyde (2.15 g, 12.5 mmol) and 3-oxo-3-thiophen-3-yl-propionic acid ethyl ester (2.97 g, 14.9 mmol) in dry ethanol (66 mL). The solution was then stirred at reflux temperature for 5 h. After completion of the reaction, the cooled suspension was filtered off and the crude yellow solid was purified by recrystallization. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | In ethanol; for 20h;Reflux; | EXAMPLE 14: Furan-Pz Coupling Moiety [00446] A furan-Pz nucleophilic trap coupling moiety was synthesized according to Scheme 14 below. heme 14 [00447] Ethyl 4-(3-(furan-3-yl)-5-oxo-4,5-dihydro-lH-pyrazol-l-yl)benzoate (Fl)- A solution of ethyl 3-(furan-3-yl)-3-oxopropanoate (1.46 mmol) and 4-hydrazinobenzoic acid hydrogen chloride was refluxed in 5.5mL ethanol for 20h. Upon cooling to room temperature, the reaction mixture was concentrated in vacuo and purified via silica gel chromatography using a 3-60% ethyl acetate:hexane gradient to yield 122.4mg of product. [00448] 1H NMR (400MHz, CDC13) 8.10 (m, 4H), 7.97 (dd, J= 1.6, 0.8 Hz, 1H), 7.55 (dd, J= 2.0, 1.6 Hz, 1H), 6.90 (dd, J= 2.0, 0.8 Hz, 1H), 4.40 (q, J = 7.2 Hz, 2H), 3.78 (s, 2H), 1.43 (t, J= 7.2 Hz, 3H). LRMS (ESI) calcd for C16H14N2O4 [M+H]+: 299; found 299. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trifluoroacetic acid; In dichloromethane; at 0℃; for 4h;Molecular sieve; Inert atmosphere; | General procedure: To a degassed mixture of PhI=NTs (0.6 mmol, 224 mg) and powdered 4 A molecular sieves (240 mg)was added dichloromethane (1 mL). The reaction was then cooled to 0 oC and solution oftrifluoroacetic acid (0.05 mmol, 3.83 muL) in dichloromethane (1 mL) was added. Successively, 1,3-dicarbonyl compounds (0.5 mmol) was added and the reactions was monitored by TLC. Uponcompletion, the reaction was filtered, washed with EtOAc and concentrated under reduced pressure toafford the crude mixture. The latter was then purified by flash chromatography (1:4 EtOAc/n-Hex aseluent) to furnish the title compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: The synthetic procedure for the preparation of individual IPO enantiomers was based on the previous work described for the synthesis of racemic IPO (Alvarez-Diez and Zheng, 2004) (Supplemental Fig. 1). In brief, ethyl-b-oxo-3-furan-propionate (100 mg, 0.55 mmol) was dissolved in anhydrous EtOH (5 mL), followed by the addition of sodium ethoxide (41 mg, 0.6 mmol) and either (R)-(+)-propylene oxide or (S)-(+)-propylene oxide (670 mg, 11.5 mmol). The mixtures were stirred for 24 hours and subsequently quenched by adjusting the pH to 7 with dilute HCl. Extraction with diethylether followed by flash chromatography yielded (R)- and (S)-furyl-gamma-lactone in 67% and 71% yields, respectively. In the second step, each respective lactone was hydrolyzed in the presence of 20 M sulfuric acid at 65C for 24 hours to yield (R)- and (S)-IPO in 43% and 33% yields, respectively. Separate fractions of the (R)- and (S)-IPO were further purified by HPLC, utilizing Shimadzu LC-10ADVP pumps coupled to a Shimadzu SPD-M10AVP photodiode array detector set to 254 nm (Shimadzu, Columbia, MD). Chromatographic separation was performed with a Keystone chiral b-OH column (150 2.0 mm, 5 mm;Thermo Hypersil, Bellefonte, PA) and a 1.5-mL/min isocratic elution composed of 15% acetonitrile/85% water for a total run time of 15 minutes. (S)- and (R)-IPO were eluted at 8.0 and 7.4 minutes, respectively, under these conditions. Collected fractions were extracted with chloroform, and the structures of the recovered enantiomers were confirmed by 1H NMR, 13C NMR, and high-resolution mass spectrometry, all of which matched previously reported spectra (Boyd et al., 1972). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: The synthetic procedure for the preparation of individual IPO enantiomers was based on the previous work described for the synthesis of racemic IPO (Alvarez-Diez and Zheng, 2004) (Supplemental Fig. 1). In brief, ethyl-b-oxo-3-furan-propionate (100 mg, 0.55 mmol) was dissolved in anhydrous EtOH (5 mL), followed by the addition of sodium ethoxide (41 mg, 0.6 mmol) and either (R)-(+)-propylene oxide or (S)-(+)-propylene oxide (670 mg, 11.5 mmol). The mixtures were stirred for 24 hours and subsequently quenched by adjusting the pH to 7 with dilute HCl. Extraction with diethylether followed by flash chromatography yielded (R)- and (S)-furyl-gamma-lactone in 67% and 71% yields, respectively. In the second step, each respective lactone was hydrolyzed in the presence of 20 M sulfuric acid at 65C for 24 hours to yield (R)- and (S)-IPO in 43% and 33% yields, respectively. Separate fractions of the (R)- and (S)-IPO were further purified by HPLC, utilizing Shimadzu LC-10ADVP pumps coupled to a Shimadzu SPD-M10AVP photodiode array detector set to 254 nm (Shimadzu, Columbia, MD). Chromatographic separation was performed with a Keystone chiral b-OH column (150 2.0 mm, 5 mm;Thermo Hypersil, Bellefonte, PA) and a 1.5-mL/min isocratic elution composed of 15% acetonitrile/85% water for a total run time of 15 minutes. (S)- and (R)-IPO were eluted at 8.0 and 7.4 minutes, respectively, under these conditions. Collected fractions were extracted with chloroform, and the structures of the recovered enantiomers were confirmed by 1H NMR, 13C NMR, and high-resolution mass spectrometry, all of which matched previously reported spectra (Boyd et al., 1972). |
Tags: 36878-91-8 synthesis path| 36878-91-8 SDS| 36878-91-8 COA| 36878-91-8 purity| 36878-91-8 application| 36878-91-8 NMR| 36878-91-8 COA| 36878-91-8 structure
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H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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