* 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.
General procedure: To a mixture of ketone (1 mmol) and aldehyde (2 mmol for Table 2; 1 mmol for Table 3), Mo10V2/SiO2 (produced 40 wt.percent: of Mo10V2 to silica19, 32.5wt.percent from ICP result, typically, the Mo content from ICP was slightly lower than expected from the preparation stoichiometry) (0.06 g, 0.085 molpercent ofMo10V2 to ketone as substrate) was added and crushed at 50 °C for appropriatetime. Completion of the reaction was monitored by TLC, using n- hexane/ethylacetate (10:4) as eluent. After completion of the reaction, 2×10 mL of ether was added to the mixture and filtered off. Catalyst was washed withether and dried for reusing. The solvent of the filtrate was evaporated then followed by chromatography to obtained pure products.
93.9%
With potassium hydroxide In ethanol at 20℃;
General procedure: As outlined in Figure 2, an aqueous solution of KOH (20percent w/v,2 mL) was added to a stirred solution of the appropriate acetophenone(1 mmol, 1 equiv) in ethanol (2 mL). The mixture was stirredat room temperature for 10 min. After complete dissolution, arylaldehyde (1 mmol, 1 equiv) was added slowly and the reactionmixture was then stirred at room temperature for 24–72 h. Aftercompletion, the mixture was cooled to 0 C on an ice bath and acidifiedwith HCl (10percent v/v aqueous solution). In most cases, the productsprecipitated out upon acidification with HCl. The crudeproduct was filtered and further purified by recrystallization fromethanol. In the cases in which no precipitate formed, the mixturewas extracted with ethyl acetate and washed with brine and water.After drying over Na2SO4, the solvent was removed by rotary evaporationto give the crude product which was further purified byeither recrystallization or automated medium performance liquidchromatography, eluting with an ethyl acetate/hexanes gradient(0–60percent).
88%
With silica-gel-supported sulfuric acid In neat (no solvent) at 65℃; for 1.5 h;
General procedure: The SSA (0.02 g) was added to a well stirred suspension of PhAc (1 mL, 0.90 g, 7.53 mmol, 1 eq.) and PhCHO (0.84 g, 7.91 mmol, 1.05 eq.) and the resulting mixture was heated at 65 °C for 1.5 h. The reaction mixture was cooled to room temperature and partitioned between brine (25 mL) and CH2Cl2 (3 × 15 mL) and solid SSA was filtered off. The SSA was washed with acetone (25 mL) to ensure desorption of product on SSA surface. The combined organic extract was washed with brine (3 × 25 mL) and the organic extract was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford the chalcone as colorless solid (1.48 g, 91percent).
85.3%
With sodium hydroxide In ethanol; water at 20℃; for 24 h;
A mixture of 4-hydroxyacetophenone (1.36 g, 10 mmol), benzaldehyde(1.3 mL, 11 mmol) and sodium hydroxide (1 g, 25 mmol)were dissolved in ethanol/water (4:1 v/v, 20 mL) and stirred atroom temperature for a period of 24 h. 10percent HCl was added toadjust the solution to pH = 3 and the product precipitated. Filtrationof the reaction mixture gave a light yellow solid product witha yield of 85.3percent.
78%
With potassium hydroxide In ethanol; water at 20℃;
General procedure: The commercially available hydroxyacetophenone (1.0 mmol) was dissolved inethanol (10ml) with 20percent aqueous potassium hydroxide solution (1ml), then theappropriate benzaldehyde (1.0 mmol) was added drop by drop to the mixture. Thesolution was stirred at room temperature for 6-12 h to prepare compounds 1-7. Thepiperidine (0.5 ml) was used as a catalyst at 80 °C to obtain compounds 8-15.Compounds 16-18 were synthesized via the condensation of the hydroxyl-protectedstarting materials and deprotected subsequently. The reaction progress was monitoredusing silica gel TLC with Petroleum ether/EtOAc as mobile phase. Upon completion,the mixture was poured into water and adjusted to pH 5, which was extracted with 3 × 30 mL of EtOAc, washed with brine, dried over anhydrous Na2SO4 and purified bychromatography (PE/EA) on silica gel.
71%
With potassium hydroxide In ethanol at 5 - 20℃; for 4 h;
A mixture of phydroxyacetophenone(4.9 mmol) and benzaldehyde (4.9mmol) in EtOH (7.5 mL) was stirred at 5 °C for 10 m. Then,a solution of KOH 40percent (34.4 mmol) was added and the reactionmixture was stirred at room temperature for 4 h. Themixture was acidified with HCl 2N until pH 7 was reached.When the chalcone precipitated, it was filtered, washed withwater and dried under reduced pressure. Yellow solid, 71percentyield, m.p. 172-174 °C. IR (KBr) 3239, 1646 cm-1; 1H NMR(CD3OD) 6.70 (d, 2H, J = 9.0 Hz, CH Ar), 7.41-7.43 (m,3H, CH Ar and HC=CH), 7.71-7.75 (m, 4H, CH Ar andHC=CH), 8.02 (d, 2H, J = 9.0 Hz, CH Ar); 13C NMR(CD3OD) 115.29 (CH Ar), 121.71 (=CHC=O), 128.43 and128.86 (CH Ar), 129.67 (O=CCAr), 130.35, 131.25 and 135.27 (CH Ar), 143.90 (C Ar),143.95 (ArCH=), 162.87(CArO), 189.49 (ArC=O).
70%
With water; sodium hydroxide In ethanol at 5 - 25℃; Inert atmosphere
General procedure: An aqueous solution of NaOH (20percent, 5mL) was added dropwise to a previously cooled mixture of selected acetophenone (5mmol) and selected (hetero)aryl aldehydes (5mmol) in EtOH (25mL) under vigorous stirring. The mixture was stirred at RT for 24–72h. After completion of the reaction (as indicated by TLC), the mixture was poured onto crushed ice and acidified with dilute HCl. The precipitated product was filtered at suction and washed to neutral filtrate. The solid was recrystallized from EtOH to get crystalline product.
69%
With sodium hydroxide In ethanol at 20℃;
Add 100 mL flask to join three-hydroxyacetophenone (2.72g, 20 mmol) and benzaldehyde (2.12g, 20mmol) added, and 20 mL of absolute ethanol, with stirring, the solid was dissolved, the reaction system as a pale yellow transparent liquid, to which was added dropwise 20percent sodium hydroxide solution 6ml, reddish-brown liquid reaction system.Stirring at room temperature, TLC tracking progress of the reaction, after the disappearance of raw materials point to stop the reaction, the reaction system was poured into ice water with dilute hydrochloric PH = 6-7, a yellow solid precipitated, filtration and drying to give a crude product, the crude product was free water was recrystallized from ethanol to give a yellow solid, mass 3.10 g (theory 4.49 g of the mass), yield 69percent.
67%
With sodium hydroxide In water at 20℃;
General procedure: Toa stirred solution of acetophenone derivatives (1 mmol) and a benzlaldehydederivatives (1 mmol) in EtOH (10mL) was added 10percentNaOH (4 mL) and the reaction mixturewas stirred for 12-24 h until the solids formed. The reaction was monitored byTLC. When the reaction completed, themixture was poured into an excessive amount of ice water. Then the products were filtrated and washed carefully with ice water and cold EtOH; the resulting chalcones were purified by crystallization from EtOH in refrigerator to givethe title compounds. (Scheme 1)
65%
With lithium hydroxide monohydrate In ethanol at 20℃; for 2.25 h;
General procedure: To an ethanol solution of the substituted acetophenones(1.0 equiv) was added LiOHH2O (1.0 equiv). The reaction mixture was stirred for 15 min at room temperature and then treated withthe desired benzaldehyde (1.2 equiv). The mixture was stirred for2 h at room temperature. The reaction mixture was quenched withH2O (100 mL) and then diluted with EtOAc (200 mL) and washedwith H2O (2 200 mL) and brine (200 mL). The organic layer wasdried with anhydrous Na2SO4 and concentrated in vacuo. The residuewas purified by column chromatography on SiO2
Reference：
[1] Journal of the American Chemical Society, 2018, vol. 140, # 3, p. 1011 - 1018
[2] Monatshefte fur Chemie, 2013, vol. 144, # 3, p. 361 - 367
[3] Journal of the Chilean Chemical Society, 2013, vol. 58, # 3, p. 1926 - 1929
[4] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 8, p. 682 - 687
[5] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 4, p. 578 - 587
[6] Medicinal Chemistry Research, 2011, vol. 20, # 2, p. 184 - 191
[7] Molecules, 2013, vol. 18, # 8, p. 10081 - 10094
[8] Journal of Medicinal Chemistry, 1998, vol. 41, # 7, p. 1014 - 1026
[9] Archiv der Pharmazie, 2007, vol. 340, # 4, p. 195 - 201
[10] Chemical and Pharmaceutical Bulletin, 2008, vol. 56, # 12, p. 1675 - 1681
[11] Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 21, p. 6124 - 6133
[12] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2013, vol. 112, p. 245 - 256
[13] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 15, p. 3602 - 3606
[14] Chemical Biology and Drug Design, 2012, vol. 80, # 4, p. 584 - 590
[15] Medicinal Chemistry, 2014, vol. 10, # 1, p. 59 - 65
[16] European Journal of Medicinal Chemistry, 2018, vol. 158, p. 286 - 301
[17] Patent: CN105837564, 2016, A, . Location in patent: Paragraph 0015
[18] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 13, p. 3098 - 3102
[19] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 19, p. 6486 - 6496
[20] Journal of Medicinal Chemistry, 1993, vol. 36, # 10, p. 1434 - 1442
[21] Biological and Pharmaceutical Bulletin, 1995, vol. 18, # 12, p. 1710 - 1713
[22] Molecular Pharmacology, 1996, vol. 49, # 6, p. 1122 - 1130
[23] Bulletin of the Chemical Society of Japan, 1934, vol. 9, p. 131,138
[24] Journal of the American Chemical Society, 1930, vol. 52, p. 2538,2539
[25] Journal of the American Chemical Society, 1955, vol. 77, p. 6667
[26] Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 11, p. 4019 - 4026
[27] Journal of Agricultural and Food Chemistry, 2007, vol. 55, # 14, p. 5697 - 5700
[28] Synthetic Communications, 2008, vol. 38, # 7, p. 1070 - 1077
[29] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 15, p. 4385 - 4388
[30] Chemistry and Biodiversity, 2010, vol. 7, # 2, p. 400 - 408
[31] Chemical and Pharmaceutical Bulletin, 2011, vol. 59, # 8, p. 984 - 990
[32] E-Journal of Chemistry, 2010, vol. 7, # 3, p. 763 - 769
[33] Heterocyclic Communications, 2012, vol. 18, # 5-6, p. 239 - 243
[34] Medicinal Chemistry Research, 2013, vol. 22, # 7, p. 3160 - 3169
[35] Molecules, 2015, vol. 20, # 7, p. 11861 - 11874
[36] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 1, p. 168 - 173
[37] Journal of Medicinal Chemistry, 2017, vol. 60, # 5, p. 1734 - 1745
[38] Medical Science Monitor, 2017, vol. 23, p. 3311 - 3317
[39] Archiv der Pharmazie, 2017, vol. 350, # 9,
[40] Journal of Agricultural and Food Chemistry, 2017, vol. 65, # 22, p. 4367 - 4377
[41] Chinese Chemical Letters, 2018, vol. 29, # 1, p. 127 - 130
[42] Oriental Journal of Chemistry, 2018, vol. 34, # 4, p. 1890 - 1897
[43] Indian Journal of Heterocyclic Chemistry, 2018, vol. 28, # 3, p. 407 - 413
2
[ 22966-19-4 ]
[ 2657-25-2 ]
Yield
Reaction Conditions
Operation in experiment
99%
With boron tribromide In dichloromethane at 55℃; for 0.5 h; Inert atmosphere; Sealed tube; Microwave irradiation
General procedure: Warning – boron tribromide is toxic, corrosive and extremelyreactive when in contact with air or water. Aflame-dried 10 mL microwave vial is loaded with the methoxy chalcone(0.4 mmol) and 7 mL of dry dichloromethane. The headspace issubsequently flushed with nitrogen gas, while the boron tribromide (3 equiv.,1.2 mmol, or 4 equiv. for dimethoxy chalcones) is quickly added underthe liquid surface with a syringe. The vial is subsequently sealed with aTeflon® cap and introduced into the microwave apparatus. The targettemperature is set at 55 °C (ramp of 5 min) and the reaction time at 30min; magnetic stirring is turned on, ‘powermax’ is turned off.Upon completion of the reaction, the mixture is poured into anErlenmeyer flask of 50 mL, to which water is added drop wise until all excess BBr3 is destroyed. Thecontents of the flask is transferred into a separating funnel, to which20 mL of a 1 N aqueous sodium hydroxide solution and 20 mL ofdiethyl ether are added. Upon vigorous shaking, the intensely yellow (or red incase of a dihydroxy chalcone) water layer is isolated and acidified with3 N hydrochloric acid. The hydroxychalcone is extracted from the resultingcloudy suspension with an equal volume of diethyl ether (2x). The organic phaseis subsequently isolated and dried over MgSO4, upon which thesolvent is evaporated, furnishing the hydroxychalcone as a solid, reddish brownpowder
Reference：
[1] Tetrahedron, 2006, vol. 62, # 17, p. 4201 - 4204
[2] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 627 - 639
[3] Journal of Organic Chemistry, 2002, vol. 67, # 18, p. 6406 - 6414
[4] Tetrahedron Letters, 1997, vol. 38, # 50, p. 8749 - 8752
[5] Journal of Organic Chemistry, 2002, vol. 67, # 6, p. 1776 - 1780
[6] Journal of Organic Chemistry, 2002, vol. 67, # 8, p. 2541 - 2547
3
[ 99-93-4 ]
[ 2657-25-2 ]
Reference：
[1] Journal of Medicinal Chemistry, 2001, vol. 44, # 25, p. 4443 - 4452
[2] Journal of Pharmacy and Pharmacology, 1997, vol. 49, # 5, p. 530 - 536
[3] Journal of Medicinal Chemistry, 1993, vol. 36, # 24, p. 3904 - 3909
[4] Patent: US5985935, 1999, A,
[5] Molecules, 2018, vol. 23, # 7,
4
[ 468060-22-2 ]
[ 2657-25-2 ]
Reference：
[1] Journal of Medicinal Chemistry, 2001, vol. 44, # 25, p. 4443 - 4452
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 24, p. 3904 - 3909
[3] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 20, p. 4632 - 4635
5
[ 99259-75-3 ]
[ 2657-25-2 ]
Reference：
[1] Molecules, 2018, vol. 23, # 7,
6
[ 16162-69-9 ]
[ 100-52-7 ]
[ 2657-25-2 ]
Reference：
[1] Journal of Pharmacy and Pharmacology, 1997, vol. 49, # 5, p. 530 - 536
7
[ 16162-69-9 ]
[ 2657-25-2 ]
Reference：
[1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 20, p. 4632 - 4635
[2] Journal of Medicinal Chemistry, 2001, vol. 44, # 25, p. 4443 - 4452
[3] Journal of Medicinal Chemistry, 1993, vol. 36, # 24, p. 3904 - 3909
Reference：
[1] Chinese Journal of Chemistry, 2015, vol. 33, # 4, p. 486 - 494
[2] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 627 - 639
10
[ 85699-00-9 ]
[ 2657-25-2 ]
Reference：
[1] Chinese Journal of Chemistry, 2015, vol. 33, # 4, p. 486 - 494
11
[ 100-06-1 ]
[ 2657-25-2 ]
Reference：
[1] European Journal of Medicinal Chemistry, 2015, vol. 101, p. 627 - 639
12
[ 140-10-3 ]
[ 108-95-2 ]
[ 2657-25-2 ]
Reference：
[1] Yakugaku Zasshi, 1954, vol. 74, p. 495[2] Chem.Abstr., 1955, p. 8182
With hydrogenchloride; sodium sulfate; In ethanol; water;Reflux;
Three-necked flask (5mmol, 642muL) of o-aminothiophenol, (5mmol, 500muL) of concentrated hydrochloric acid, 20ml of absolute ethanol, (5mmol, 1.12g) (E) -1- (4- hydroxyphenyl) -3 - (phenyl) prop-2-en-1-one, (5mmol, 0.71g) over anhydrous sodium sulfate, heated to reflux, (P / E = 2: 1) TLC trace reaction, the reaction is stopped 7h, the reaction solution poured into water, stirred for 5min, solid precipitated, suction filtration, dried and then recrystallized to give a white solid 0.1.36g, 82percent yield.
With hydrogenchloride; sodium hydroxide; benzaldehyde; In ethanol; water;
19) Preparation of 4'-hydroxychalcone STR28 2.7 g (20 mmol) of 4hydroxyacetophenone and 2.1 g (20 mmol) of benzaldehyde were added to a solution of 12 g of sodium hydroxide in 10 ml of water and 50 ml of ethanol, and the solution was refluxed for 3 h. After addition of 50 mnl of water, the solution was acidified with 90 ml of 4M hydrochloric acid and extracted with 100 ml of ether. The organic phase was dried (MgSO4) and concentrated in vacuo to give 4.82 g of a gum, from which 0.124 g of 4'-hydroxychalcone identical with that previously decribed by R, L.
(3-Cyano-4-phenyl-6-{4-[1-phenyl-meth-(E)-ylidene-hydrazinocarbonylmethoxy]-phenyl}-pyridin-2-ylsulfanyl)-acetic acid [1-phenyl-meth-(E)-ylidene]-hydrazide[ No CAS ]
(6-{4-[1-(4-Chloro-phenyl)-meth-(E)-ylidene-hydrazinocarbonylmethoxy]-phenyl}-3-cyano-4-phenyl-pyridin-2-ylsulfanyl)-acetic acid [1-(4-chloro-phenyl)-meth-(E)-ylidene]-hydrazide[ No CAS ]
(3-Cyano-6-{4-[1-(4-methoxy-phenyl)-meth-(E)-ylidene-hydrazinocarbonylmethoxy]-phenyl}-4-phenyl-pyridin-2-ylsulfanyl)-acetic acid [1-(4-methoxy-phenyl)-meth-(E)-ylidene]-hydrazide[ No CAS ]
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃;Inert atmosphere;
General procedure: A solution of diisopropyl azodicarboxylate (DIAD) (18.14 mmol, 2.86 mL) in dry THF (10 mL) was added dropwise to a stirred solution of the alcohols 11-13 (13.30 mmol), triphenylphosphine (4.76 g, 18.14 mmol), and appropriate phenols (18.14 mmol) in dry THF (40 mL) under nitrogen atmosphere. After stirring for 10-12 h at room temperature, the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent cyclohexane/ethyl acetate 8:2) to afford 17-34 esters.
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃;Inert atmosphere;
General procedure: A solution of diisopropyl azodicarboxylate (DIAD) (18.14 mmol, 2.86 mL) in dry THF (10 mL) was added dropwise to a stirred solution of the alcohols 11-13 (13.30 mmol), triphenylphosphine (4.76 g, 18.14 mmol), and appropriate phenols (18.14 mmol) in dry THF (40 mL) under nitrogen atmosphere. After stirring for 10-12 h at room temperature, the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent cyclohexane/ethyl acetate 8:2) to afford 17-34 esters.
ethyl 2-[4-(3-hydroxypropyl)phenoxy]-2-methylpropanoate[ No CAS ]
[ 2657-25-2 ]
[ 1415608-83-1 ]
Yield
Reaction Conditions
Operation in experiment
65%
With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20℃;Inert atmosphere;
General procedure: A solution of diisopropyl azodicarboxylate (DIAD) (18.14 mmol, 2.86 mL) in dry THF (10 mL) was added dropwise to a stirred solution of the alcohols 11-13 (13.30 mmol), triphenylphosphine (4.76 g, 18.14 mmol), and appropriate phenols (18.14 mmol) in dry THF (40 mL) under nitrogen atmosphere. After stirring for 10-12 h at room temperature, the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent cyclohexane/ethyl acetate 8:2) to afford 17-34 esters.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
