Reaxys
PubChem
eMolecules
Reactions (4)
Yield
Substances (5)
Citations (5)
Conditions
References
1
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Rx-ID: 41693117 Find similar reactions
50%
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Stage #1: benzeneacetic acid methyl ester With lithium hexamethyldisilazane in tetrahydrofuran
T=-78°C; 0.333333 h; Stage #2: acetic anhydride in tetrahydrofuran
T=-78 - 0°C; Hide Experimental Procedure
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CARDIOXYL PHARMACEUTICALS, INC.; THE JOHNS HOPKINS UNIVERSITY; KALISH, Vincent, J.; BROOKFIELD, Frederick, A.; COURTNEY, Stephen, M.; FROST, Lisa, M.; TOSCANO, John, P.; GUTHRIE, Daryl, A.; NORTH, Carl, L.
Patent: WO2015/183839 A1, 2015 ; Location in patent: Page/Page column 184; 185; 193; 194; 219 ; Title/Abstract Full Text Show Details
6.1; 24.1:6.1 Methyl 3-oxo-2-phenylbutanoate
General procedure: General Method 13: Phenylbutanoate Synthesis:_To a solution of an alkyl phenyl acetate (1 equiv) in THF (10 vol) in a flask at a temperature of about -78°C (dry ice-acetone bath) was added 1M lithium 1,1,1,3,3,3-hexamethyldisilazan-2-ide in THF (2 equiv). The reaction mixture was stirred for about 20 minutes at about -78°C. Acetic anhydride (1 equiv) was added rapidly, the flask was removed from the dry ice-acetone bath and placedinto an ice-water bath where it was allowed to warm to about 0°C, and stirred until substantially complete consumption of the starting material was achieved as determined by LC-MS. The mixture was quenched with ammonium chloride solution (10 vol) and the product was extracted into ethyl acetate (3 x 10 vol). The ethyl acetate layers were combined, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide a product which was chromatographed by silica gelcolumn chromatography eluting with 0-100percent ethyl acetate:heptanes gradients.:_Methyl 3 -oxo-2-phenylbutanoate was synthesized from methyl 2 -phenylacetate according to General Method 13 and was chromatographed by silica gel column chromatography (12percent ethyl acetate in heptanes) to provide the title compound as a pale yellow oil (22 g, 50percent yield). LC-MS:tR—l.13/l.16 mi [M+H] =193.
2
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Rx-ID: 4661188 Find similar reactions
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51%
With potassium tert-butylate in tetrahydrofuran
T=-78 - 45°C; 13 h; Inert atmosphere;
Ashida, Yuichiro; Sato, Yuka; Suzuki, Takeyuki; Ueno, Kanako; Kai, Ken-Ichiro; Nakatsuji, Hidefumi; Tanabe, Yoo
Chemistry - A European Journal, 2015 , vol. 21, # 15 p. 5934 - 5945 Title/Abstract Full Text View citing articles Show Details
39%
With potassium tert-butylate
1.) -78 deg C, 2 h, 2.) r.t., 18 h; reflux,1 h;
Thuring, Jan Willem J. F.; Van Gaal, Angelique A. M. A.; Hornes, Sander J.; De Kok, Margreet M.; Nefkens, Gerard H. L.; Zwanenburg, Binne
Journal of the Chemical Society - Perkin Transactions 1, 1997 , # 5 p. 767 - 774 Title/Abstract Full Text View citing articles Show Details
A
B
C
D
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3
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Rx-ID: 1581971 Find similar reactions
A: 23.9 % Chromat. C: 12.5 % Chromat. D: 27.2 % Chromat.
in 1,4-dioxane
T=10°C; Irradiationalso thermolysis at 80 deg C, other 2-diazo-1,3-dicarbonyl compounds; Product distributionMechanism;
4
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Rx-ID: 7810846
Tomioka, Hideo; Hayashi, Norihiro; Asano, Tsuneo; Izawa, Yasuji
Bulletin of the Chemical Society of Japan, 1983 , vol. 56, # 3 p. 758 - 761 Title/Abstract Full Text Show Details
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Phenylessigsaeure-methylester, AcOMe, NaH, AcOH;
Aspro-Nicholas Ltd.
Patent: GB1088846 , 1963 ; Chem.Abstr., 1968 , vol. 68, # 105193x Full Text Show Details