- Production process of 2-methyl-2-(4-chlorphenyl)-1, 3-propylene glycol
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The invention discloses a production process of 2-methyl-2-(4-chlorphenyl)-1, 3-propylene glycol. The process comprises the following steps: taking p-chloroiodobenzene and diethyl malonate as initialraw materials; firstly, subjecting the p-chloroiodobenzene and diethyl malonate to coupling reaction to prepare a compound 3; carrying out alkylation reaction on the compound 3 and methyl iodide to obtain a compound 4; reacting the compound 4 with lithium aluminum hydride to obtain a 2-methyl-2-(4-chlorphenyl)-1, 3-propylene glycol crude product; and finally, subjecting the 2-methyl-2-(4-chlorphenyl)-1, 3-propylene glycol to a recrystallization procedure, thus obtaining the target product 2-methyl-2-(4-chlorphenyl)-1, 3-propylene glycol.
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Paragraph 0023-0026
(2020/07/12)
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- OXIDATIVE COUPLING OF ARYL BORON REAGENTS WITH SP3-CARBON NUCLEOPHILES, AND AMBIENT DECARBOXYLATIVE ARYLATION OF MALONATE HALF-ESTERS VIA OXIDATIVE CATALYSIS
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Described herein are methods of oxidative coupling of aryl boron reagents with sp3-carbon nucleophiles, and ambient decarboxylative arylation of malonate half-esters via oxidative catalysis.
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Paragraph 0142; 0143; 0176
(2018/07/29)
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- Oxidative Coupling of Aryl Boron Reagents with sp3-Carbon Nucleophiles: the Enolate Chan-Evans-Lam Reaction
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Reported is a versatile new oxidative method for the arylation of activated methylene species. Under mild reaction conditions (RT to 40 C), Cu(OTf)2 mediates the selective coupling of functionalized aryl boron species with a variety of stabilized sp3-nucl
- Moon, Patrick J.,Halperlin, Heather M.,Lundgren, Rylan J.
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supporting information
p. 1894 - 1898
(2016/08/31)
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- Oxidative coupling of aryl boron reagents with sp3-carbon nucleophiles: The enolate chan–evans–lam reaction
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Reported is a versatile new oxidative method for the arylation of activated methylene species. Under mild reaction conditions (RT to 40°C), Cu(OTf)2mediates the selective coupling of functionalized aryl boron species with a variety of stabilized sp3-nucleophiles. Tertiary malonates and amido esters can be employed as substrates to generate quaternary centers. Complementing either traditional cross-coupling or SNAr protocols, the transformation is chemoselective in the presence of halogen electrophiles, including aryl bromides and iodides. Substrates bearing amide, sulfonyl, and phosphonyl groups, which are not amenable to coupling under mild Hurtley-type conditions, are suitable reaction partners.
- Moon, Patrick J.,Halperin, Heather M.,Lundgren, Rylan J.
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supporting information
p. 1894 - 1898
(2016/12/03)
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- An efficient method for the preparation of mono α-aryl derivatives of diethyl malonate and ethyl cyanoacetate using ethyl-1-imidazole carbamate (EImC)
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An efficient method for the synthesis of mono α-aryl derivatives of diethyl malonate and ethyl cyanoacetate using ethyl-1-imidazole carbamate (EImC) has been described. Using this method many sterically hindered and highly substituted mono α-aryl derivatives of diethyl malonate and ethyl cyanoacetate were synthesized in high yield.
- Behera, Manoranjan,Venkat Ragavan,Sambaiah,Erugu, Balaiah,Rama Krishna Reddy,Mukkanti,Yennam, Satyanarayana
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experimental part
p. 1060 - 1062
(2012/03/26)
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- 3-aryl-6-methoxy-2-oxo-1,2-dihydroquinoline-4-carbonitriles as solvent and pH independent green fluorescent dyes
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Highly fluorescent and stable 3-aryl-6-methoxy-2-oxoquinoline-4- carbonitriles 6 (λexc = 408 nm and λem = 510 nm) were synthesized starting from appropriate arylmalonates 2. Ring closure reaction with p-anisidine gave 4-hydroxyquinol
- Enoua, Guy Crepin,Uray, Georg,Stadlbauer, Wolfgang
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p. 1415 - 1421
(2013/02/22)
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- Synthesis of optically active heterocyclic compounds by preparation of 1,3-dinitro derivatives and enzymatic enantioselective desymmetrization of prochiral diamines
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A general approach for the highly efficient chemical preparation of novel optically active 2-substituted propane-1,3-diamines is described. Diamines have been obtained from the corresponding commercially available aldehydes in a straightforward, two-step synthesis via the corresponding 1,3-dinitro compounds, which were hydrogenated under mild reaction conditions by using platinum dioxide as the catalyst. Subsequent enzymatic enantioselective desymmetrization mediated by Pseudomonas cepacia lipase allowed the recovery of a family of monocarbamates in good to high, enantiomeric excesses (70-90% ee).
- Rios-Lombardia, Nicolas,Busto, Eduardo,Gotor-Fernandez, Vicente,Gotor, Vicente
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supporting information; experimental part
p. 484 - 493
(2010/04/28)
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- Process for Preparing 2-Arylcarbonyl Compounds, 2-Aryl Esters and 2-Arylnitriles and their Heteroaromatic Analogues
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Process for preparing compounds by cross-coupling of enolizable carbonyl compounds, nitriles or their analogues with substituted aryl or heteroaryl compounds in the presence of a Br?nsted base and of a catalyst or precatalyst containing a.) a transition m
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Page/Page column 5
(2008/12/08)
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- 2,4-DIAMINOQUINAZOLINES FOR SPINAL MUSCULAR ATROPHY
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2,4-Diaminoquinazolines of formulae I-IV and VI (I, II, III, IV and VI) are useful for treating spinal muscular atrophy (SMA).
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- A general and mild copper-catalyzed arylation of diethyl malonate
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Chemical equation presented A general method for the synthesis of α-aryl malonates is described. The coupling of an aryl iodide and diethyl malonate in the presence of Cs2CO3 and catalytic amounts of copper(I) iodide and 2-phenylphenol affords the α-aryl malonate in good to excellent yields. The mild reaction conditions and high levels of functional group compatibility make this an attractive synthetic alternative to previous methods.
- Hennessy, Edward J.,Buchwald, Stephen L.
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p. 269 - 272
(2007/10/03)
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- Chemoenzymatic enantioselective synthesis of baclofen
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We report two different chemoenzymatic enantioselective syntheses of baclofen based on the distinction between enantiotopic ester groups in compounds bearing a prochiral centre. In the first approach, the key step is the highly stereoselective enzymatic hydrolysis of dimethyl 3-(4-chlorophenyl)glutarate by chymotrypsin in an aqueous medium. In the second approach, the key step is the enzyme-catalyzed esterification of 2-(4-chlorophenyl)-1,3-propanediol by acetic anhydride in the presence of a lipase in an organic medium. We report two different chemoenzymatic enantioselective syntheses of baclofen based on the distinction between enantiotopic ester groups in compounds bearing a prochiral centre. In the first approach, the key step is the highly stereoselective enzymatic hydrolysis of dimethyl 3-(4-chlorophenyl)glutarate by chymotrypsin in an aqueous medium. In the second approach, the key step is the enzyme-catalyzed esterification of 2-(4-chlorophenyl)-1,3-propanediol by acetic anhydride in the presence of a lipase in an organic medium.
- Chenevert,Desjardins
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p. 2312 - 2317
(2007/10/02)
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- AROMATIC NUCLEOPHILIC SUBSTITUTION ON η6-Cr(CO)3-COMPLEXED HALOGENOARENES: ARYLATION OF SECONDARY CARBANIONS
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The paper deals with the aromatic nucleophilic substitution on η6-Cr(CO)3-complexed fluorobenzene and ortho-, meta-, and para-dichlorobenzenes with stabilized carbanions, both under phase-transfer conditions (PTC) and in DMSO solution.In the case of the η6-Cr(CO)3-complexed ortho-, meta-, and para-dichlorobenzenes only one chlorine atom is replaced by the carbanions.
- Baldoli, Clara,Buttero, Paola Del,Licandro, Emanuela,Maiorana, Stefano
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p. 409 - 414
(2007/10/02)
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- ARYLATION OF DIETHYL MALONATE VIA NUCLEOPHILIC SUBSTITUTION REACTIONS WITH CYCLOPENTADIENYLIRON COMPLEXES OF CHLOROARENES
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Reaction of an η6-chloroarene-η5-cyclopentadienyliron hexafluorophosphate with diethyl malonate in the presence of K2CO3 in THF/DMSO gave a corresponding SNAr product, η6-diethyl arylmalonate-η5-cyclopentadienyliron hexafluorophosphate, which, upon pyrolic sublimation, resulted in the liberation of the arylated malonic ester.Such esters prepared in the present work included RPhCH(COOEt)2, with R = o-, m- or p-CH3, 2,6-(CH3)2, or o-, m- or p-Cl.
- Abd-El-Aziz, Alaa S.,Lee, Choi Chuck,Piorko, Adam,Sutherland, Ronald G.
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p. 291 - 300
(2007/10/02)
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