20026-96-4|Ethyl 3-(4-chlorophenyl)propiolate| Ambeed

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Quality Control of [ 20026-96-4 ] Purity: 97% SDS Specification

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Product Details of [ 20026-96-4 ]

CAS No. :	20026-96-4
Formula :	C₁₁H₉ClO₂
M.W :	208.64
SMILES Code :	O=C(OCC)C#CC1=CC=C(Cl)C=C1
MDL No. :	MFCD00456510
Boiling Point :	No data available
InChI Key :	PSAMQLWFJMRMOG-UHFFFAOYSA-N
Pubchem ID :	641307

Safety of [ 20026-96-4 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P280-P305+P351+P338

Application In Synthesis of [ 20026-96-4 ]

* 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.

Downstream synthetic route of [ 20026-96-4 ]

[ 20026-96-4 ] Synthesis Path-Downstream 1~35

1
[ 39910-98-0 ]
[ 20026-96-4 ]
[ 73350-21-7 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1979,vol. 321,p. 899 - 904.

2
[ 20026-96-4 ]
[ 1774-47-6 ]
[ 19966-66-6 ]

References: [1]Chemical and pharmaceutical bulletin,1968,vol. 16,p. 784 - 792.

3
[ 20026-96-4 ]
[ 14723-58-1 ]

References: [1]Chemical and pharmaceutical bulletin,1966,vol. 14,p. 1277 - 1286.

4
[ 20026-96-4 ]
[ 17356-08-0 ]
[ 20621-88-9 ]

References: [1]Chemical and pharmaceutical bulletin,1968,vol. 16,p. 1351 - 1359.

5
[ 765-43-5 ]
[ 20026-96-4 ]
[ 76209-49-9 ]

References: [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 941 - 944.

6
[ 20026-96-4 ]
[ 10268-06-1 ]
4-(4-Chloro-phenyl)-3-(2-chloro-phenyl)-3H-pyridine-2,6-dione [ No CAS ]

References: [1]Australian Journal of Chemistry,1988,vol. 41,p. 1717 - 1726.

7
[ 20026-96-4 ]
[ 5323-87-5 ]
3-Ethoxy-6-(4-chlorophenylpropiolyl)-2-cyclohexen-1-one [ No CAS ]

References: [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 941 - 944.

8
[ 20026-96-4 ]
[ 20101-92-2 ]
3,4-Bis-(4-chloro-phenyl)-3H-pyridine-2,6-dione [ No CAS ]

References: [1]Australian Journal of Chemistry,1988,vol. 41,p. 1717 - 1726.

9
[ 20026-96-4 ]
[ 58357-84-9 ]
3-(3-Chloro-phenyl)-4-(4-chloro-phenyl)-3H-pyridine-2,6-dione [ No CAS ]

References: [1]Australian Journal of Chemistry,1988,vol. 41,p. 1717 - 1726.

10
[ 20026-96-4 ]
[ 3240-10-6 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 2461 - 2466.
[2]Chemical Communications,2015,vol. 51,p. 13004 - 13007.
[3]Angewandte Chemie - International Edition,2017,vol. 56,p. 1026 - 1030.
Angew. Chem.,2017,p. 1046 - 1050,5.
[4]Organic Letters,2018,vol. 20,p. 1066 - 1069.

11
[ 35282-97-4 ]
[ 20026-96-4 ]

References: [1]Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy,1982,vol. 38,p. 649 - 654.

12
[ 40886-60-0 ]
[ 20026-96-4 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 1727 - 1732.
[2]Australian Journal of Chemistry,1988,vol. 41,p. 1717 - 1726.

13
[ 20026-96-4 ]
[ 103-81-1 ]
[ 58357-90-7 ]

References: [1]Australian Journal of Chemistry,1988,vol. 41,p. 1717 - 1726.

Yield	Reaction Conditions	Operation in experiment
4.60 g (100%)		12-4: Ethyl 4-chlorophenylpropiolate (A) Prepared in a similar fashion from 4-chloroiodobenzene to provide 4.60 g (100%) of a colourless solid.

17
[ 855784-94-0 ]
[ 20026-96-4 ]
6-(4-chloro-3-methylphenyl)-3-[(3-(4-chlorophenyl)-5-oxo-2,5-dihydro-pyrazol-1-yl)carbonylmethoxy]pyridazine [ No CAS ]

References: [1]Canadian Journal of Chemistry,2005,vol. 83,p. 251 - 259.

18
[ 83501-15-9 ]
[ 20026-96-4 ]

References: [1]Synlett,2008,p. 443 - 447.

19
[ 20026-96-4 ]
[ 131292-29-0 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 2461 - 2466.

20
[ 20026-96-4 ]
[ 42122-34-9 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 2461 - 2466.

21
[ 20026-96-4 ]
ethyl 5-(4-chlorophenyl)penta-2,4-diynoate [ No CAS ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 2461 - 2466.

22
[ 20026-96-4 ]
[ 131292-05-2 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 2461 - 2466.

23
[ 122-01-0 ]
[ 20026-96-4 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1994,p. 1727 - 1732.
[2]Patent: WO2012/67664,2012,A1 .

24
[ 20026-96-4 ]
[ 20621-93-6 ]

References: [1]Chemical and pharmaceutical bulletin,1968,vol. 16,p. 1351 - 1359.

25
[ 20026-96-4 ]
Dimethyloxosulfonium-1-phenylcarbamoyl-3-ethoxycarbonyl-2-(p-chlor-phenyl)-allylid [ No CAS ]

References: [1]Chemical and pharmaceutical bulletin,1968,vol. 16,p. 784 - 792.

26
[ 1679-18-1 ]
[ 623-47-2 ]
[ 20026-96-4 ]

References: [1]Tetrahedron Letters,2009,vol. 50,p. 5044 - 5046.
[2]Organic Letters,2017,vol. 19,p. 316 - 319.
[3]Chemical Communications,2014,vol. 50,p. 2488 - 2490.

27
[ 20026-96-4 ]
[ 93102-05-7 ]
[ 1229236-32-1 ]

Yield	Reaction Conditions	Operation in experiment
79%		To a solution of <strong>[20026-96-4](4-chloro-phenyl)-propynoic acid ethyl ester</strong> (92.65 g, 444.1 mmol) in dichloromethane (425 mL) was added trifluoroacetic acid (3.4, 44.4 mmol). The reaction mixture was cooled with a water bath and a solution of N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (164.7 g, 666.1 mmol) in dichloromethane (325 mL) was added dropwise over a period of 1.5 h. It was stirred for 22 h at ambient temperature. Further N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (27.5 g, 111.0 mmol) in dichloromethane (50 mL) was added and stirring was continued for 2 h at ambient temperature. The solvent was distilled off and the residue was taken up in dioxane (950 mL). After addition of water (475 mL) and sodium hydroxide (32%, 114.3 mL, 1.23 mol), it was stirred for 67 h at ambient temperature. After concentration the residue was diluted with water (400 mL) and extracted with tert-butylmethylether (400 mL). The organic layers were washed with water (400 mL). The aqueous layers were combined, cooled to 5 C. and set to pH=1.5 with aqueous HCl (25%, 172). After stirring for 1 h at 5 C., the solid was filtered off and was washed with water (1400 mL) and ethanol (400 mL). Drying (50 C., 25 mbar) afforded the title compound (109.85 g, 79%) as an off-white solid. MS m/e: 312.2/314.1 [M-H]-.
79%		b) l-Benzyl-4-(4-chloro-phenyl)-2,5-dihydro-lH-pyrrole-3-carboxylic acidTo a solution of <strong>[20026-96-4](4-chloro-phenyl)-propynoic acid ethyl ester</strong> (92.65 g, 444.1 mmol) in dichloromethane (425 mL) was added trifluoro acetic acid (3.4, 44.4 mmol). The reaction mixture was cooled with a water bath and a solution of N-(methoxymethyl)-N- (trimethylsilylmethyl)benzylamine (164.7 g, 666.1 mmol) in dichloromethane (325 mL) was added dropwise over a period of 1.5 h. It was stirred for 22 h at ambient temperature. Further N- (methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (27.5 g, 111.0 mmol) indichloromethane (50 mL) was added and stirring was continued for 2 h at ambient temperature. The solvent was distilled off and the residue was taken up in dioxane (950 mL). After addition of water (475 mL) and sodium hydroxide (32%, 114.3 mL, 1.23 mol), it was stirred for 67 h at ambient temperature. After concentration the residue was dilluted with water (400 mL) and extracted with tert-butylmethylether (400 mL). The organic layers were washed with water (400 mL). The aqueous layers were combined, cooled to 5 C and set to pH=1.5 with aqueous HC1 (25 %, 172). After stirring for 1 h at 5 C, the solid was filtered off and was washed with water (1400 mL) and ethanol (400 mL). Drying (50 C, 25 mbar) afforded the title compound (109.85 g, 79%) as an off-white solid. MS m/e: 312.2/314.1 [M-H]
60%		b) 1-Benzyl-4-(4-chloro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid (IIa) At r.t., a solution of N-(methoxymethyl)-N-(phenylmethyl)-N-(trimethylsilyl)methyl amine (116.8 g, 0.49 mol) in CH2Cl2 (260 ml) was added dropwise over 90 min to a stirred solution of <strong>[20026-96-4](4-chloro-phenyl)-propynoic acid ethyl ester</strong> (72.0 g, 0.34 mol) and trifluoroacetic acid (2.5 ml, 0.03 mol) in CH2Cl2 (350 ml). The reaction mixture was stirred at 25 C. overnight and afterwards evaporated to dryness. The residue was dissolved in dioxane (0.8 l); an aqueous solution of NaOH (91.0 ml, 1.02 mol, 3 eq.) was added, and the resulting emulsion was stirred at r.t. for 48 h. The low boiling organic solvent was removed under vacuum, water (0.9 l) was added, and the aqueous layer was separated and washed with TBME (1 l). The aqueous layer was then acidified to a pH value of 2.5 by addition of 25% HCl. The resulting suspension was stirred overnight; the white precipitate was filtered off, washed with water and ethanol and dried under high vacuum to yield 62.0 g (60%) of IIa as a white solid. ES-MS m/e: 312.4 (M-H+).

References: [1]Patent: US2011/144081,2011,A1 .Location in patent: Page/Page column 46.
[2]Patent: WO2011/85886,2011,A1 .Location in patent: Page/Page column 92.
[3]Patent: US2010/152462,2010,A1 .Location in patent: Page/Page column 4.

28
[ 637-87-6 ]
[ 623-47-2 ]
[ 20026-96-4 ]

Yield	Reaction Conditions	Operation in experiment
61%		a) (4-Chloro-phenyl)-propynoic acid ethyl ester (Va) Under argon atmosphere, a four neck flask was charged with 1-chloro-4-iodo-benzene (130.0 g, 0.55 mol), bis(triphenylphosphine) palladium(II) chloride (7.57 g, 10.8 mmol, 2 mol %), copper(I) iodide (4.19 g, 22.0 mmol, 4 mol %) and dry THF (1.4 l). At r.t., cesium carbonate (355.3 g, 1.09 mol, 2 eq.) was added over 5 min. Afterwards propynoic acid ethyl ester (111.3 ml, 1.09 mol, 2 eq.) was added, and the reaction mixture was stirred overnight at 35 C. An additional portion of propynoic acid ethyl ester (11.1 ml, 0.11 mol, 0.2 eq.) was added, and the reaction was stirred for another 3 h at 35 C. The reaction mixture was evaporated to dryness, and the residue was taken up in toluene (0.5 l) and heptane (1 l). The resulting suspension was stirred at 40 C. for 1 h and filtered over celite. The filtrate was concentrated, and the product purified by silica gel filtration (toluene/heptane 1:2) to yield 72.6 g (61%) of Va as a light yellow solid.
	With copper(l) iodide; caesium carbonate;bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 35℃; for 41h;Inert atmosphere;	A mixture of 1-chloro-4-iodobenzene (120.4 g, 0.50 mol) and cesium carbonate (352.8 g, 1.0 mol) in tetrahydrofuran (1.275 L) was evaporated and flushed with argon. Then cuprous iodide (3.81 g, 20.0 mmol) and bis(triphenylphosphine)palladium(II) chloride (7.02 g, 10.0 mmol) were added and then ethyl propiolate (100 g, 1.01 mol) was added dropwise over a period of 20 min. The resulting dark brown suspension was stirred for 41 h at 35 C., then filtrated over Hyflo and washed with THF (5 L). The solution was concentrated and treated with toluene /heptane 1:2 (1.5 L) and stirred for 1 h at 45 C. under reduced pressure (250 mbar). The resulting suspension was filtered and the residue was washed with further toluene /heptane 1:2 (1.5 L). The solid was dried affording 181.64 g (MS m/e: 209.0/211.2 [M+H]+) of a dark brown oil as crude product which was used without further purification.
	With caesium carbonate;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; at 35℃; for 41.3333h;Inert atmosphere;	a) (4-Chloro-phenyl)-propynoic acid ethyl esterA mixture of l-chloro-4-iodobenzene (120.4 g, 0.50 mol) and cesium carbonate (352.8 g, 1.0 mol) in tetrahydrofuran (1.275 L) was evaporated and flushed with argon. Then cuprous iodide (3.81 g, 20.0 mmol) and bis(triphenylphosphine)palladium(II) chloride (7.02 g, 10.0 mmol) were added and then ethyl propiolate (100 g, 1.01 mol) was added dropwise over a period of 20 min. The resulting dark brown suspension was stirred for 41 h at 35 C, then filtrated over Hyflo and washed with THF (5 L). The solution was concentrated and treated with toluene/heptane 1 :2 (1.5 L) and stirred for 1 h at 45 C under reduced pressure (250 mbar). The resulting suspension was filtered and the residue was washed with further toluene/heptane 1 :2 (1.5 L). The solid was dried affording 181.64 g (MS m/e: 209.0/211.2 [M+H]+) of a dark brown oil as crude product which was used without further purification.

References: [1]Patent: US2010/152462,2010,A1 .Location in patent: Page/Page column 4.
[2]Patent: US2011/144081,2011,A1 .Location in patent: Page/Page column 45-46.
[3]Patent: WO2011/85886,2011,A1 .Location in patent: Page/Page column 91-92.
[4]Organic Letters,2013,vol. 15,p. 4888 - 4891.
[5]Organic Letters,2014,vol. 16,p. 2606 - 2609.
[6]Organic Letters,2015,vol. 17,p. 2522 - 2525.
[7]Angewandte Chemie - International Edition,2017,vol. 56,p. 885 - 888.
Angew. Chem.,2017,vol. 129,p. 903 - 906,4.
[8]Advanced Synthesis and Catalysis,2017,vol. 359,p. 4062 - 4066.
[9]Organic Letters,2018,vol. 20,p. 1066 - 1069.

29
[ 1298131-29-9 ]
[ 1679-18-1 ]
[ 20026-96-4 ]
[ 1298131-49-3 ]

References: [1]Chemical Communications,2011,vol. 47,p. 4282 - 4284.

30
[ 623-47-2 ]
[ 20026-96-4 ]

References: [1]Chemical Communications,2011,vol. 47,p. 4282 - 4284.

31
[ 20026-96-4 ]
[ 862283-69-0 ]