Tag: M.W=100-200

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 61644-18-6, name is Chloromethyl isobutyrate, A new synthetic method of this compound is introduced below., Application In Synthesis of Chloromethyl isobutyrate

General procedure: To a solution of Compound 54B (150 mg, 0.24 mmol) in DMF (10 mL) was added chloromethyl isobutyrate (36 mg, 0.24 mmol) and Na2CO3 (50 mg, 0.48 mmol). The reaction mixture was stirred at 50 C for 3 hour. After cooling down to room temperature, the mixture was diluted with water (50 mL) and extracted with ethyl acetate (20 mL x 3). The combined extracts were washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to furnish Compound 54C. LC-MS (ESI) m/z: non-ionizable compound under routine conditions used.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
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Some common heterocyclic compound, 14920-81-1, name is Methyl 2,6-dimethylbenzoate, molecular formula is C10H12O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. name: Methyl 2,6-dimethylbenzoate

General procedure: To a flame-dried 250 mL round-bottom flask under argon wereadded 4 (8.02 g, 28.4 mmol, 1 equiv), TMEDA (8.71 mL, 58.2mmol, 2.05 equiv), and anhydrous n-hexane (28 mL). Theresulting solution was cooled in an ice bath and sec-butyllithium(1.4 M solution in cyclohexane, 42.0 mL, 58.2 mmol, 2.05equiv) was added dropwise. The ice bath was removed and thereaction mixture was stirred at room temperature for 4 h. Thereaction was cooled to -78 C and a solution of methyl 2,4,6-trimethylbenzoate (5.11 g, 28.7 mmol, 1.01 equiv) in anhydrousn-hexane (28 mL) was added slowly via cannula. After the addition,the mixture was allowed to slowly warm to room temperatureand stirred for 12 h. The reaction was quenched with water(25 mL) and the biphasic mixture was stirred vigorously for 30min. The mixture was diluted with Et2O (100 mL) and the layerswere separated. The organic layer was washed with water(2 × 150 mL) and brine (1 × 150 mL). The organic layer wastransferred to a 250 mL round-bottom flask equipped with astir bar. To the vigorously stirred solution was added conc. HCl(12 mL), resulting in a bright-yellow precipitate. The suspensionwas stirred vigorously for 30 min then diluted with water (150mL). The layers were separated and the organic layer wasextracted with water (3 × 150 mL or until the washings becomecolorless). To the combined aqueous layers was added solidNaBF4 (9.35 g, 85.2 mmol, 3 equiv), resulting in a bright-yellowprecipitate. The resulting suspension was extracted withdichloromethane (3 × 150 mL or until the washings become colorless).To the combined organic layers was added HBF4·Et2Ocomplex (3.46 mL, 28.4 mmol, 1 equiv). The solution wasswirled to achieve homogeneity then washed with water(1 × 100 mL) and aq. NaBF4 (1 M, 1 × 100 mL). The organic layerwas dried over solid NaBF4, filtered, and concentrated to dryness.The residue was purified by trituration with hexanes andfiltered. The solid was rinsed with n-pentane and dried in vacuoto give xanthylium 3 (10.6 g, 21.3 mmol, 75% yield) as a yelloworangesolid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14920-81-1, its application will become more common.

Reference:
Article; White, Alexander R.; Wang, Leifeng; Nicewicz, David A.; Synlett; vol. 30; 7; (2019); p. 827 – 832;,
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Application of 89-91-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 89-91-8 name is Methyl 2,2-dimethoxyacetate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

STR12 A mixture of methyl dimethoxyacetate (1) (8 mL, 65.5 mmol), glyoxylic acid monohydrate (5.8 g, 63 mmol) and p-toluenesulfonic acid monohydrate (60 mg, 0.32 mmol) was heated at 80 C. for 18 h. The resulting solution was cooled to 0 C. and phosphorus pentoxide (7.0 g, 49.3 mmol) was added. After heating for 4 h at 80 C., methyl glyoxylate (2) (7.9 g, 90 mmol) was obtained by distillation in 70% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2,2-dimethoxyacetate, and friends who are interested can also refer to it.

Reference:
Patent; Akzo Nobel, N.V.; US6150548; (2000); A;,
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In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 18595-14-7, name is Methyl 4-amino-3-methylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. category: esters-buliding-blocks

TEA (1.2 mmol) and the commercially available benzoyl chloride (1.1 mmol) wereadded at 000 to a solution of the corresponding aniline (1 mmol) in DCM (0.16M). The reaction mixture was left stirring at room temperature for 2h. Sat. solution of NaHCO3 (500m1) was added. The phases were separated and the aqueous layer was extracted with DCM (3 times). The combined organic layers were evaporated and purified by flash chromatography eluting with DCM/EtOAc to obtain the compounds of examples16-18,20,21 reported in Table 4.

The synthetic route of 18595-14-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROTTAPHARM BIOTECH S.R.L.; ARTUSI, Roberto; CASELLI, Gianfranco; ROVATI, Lucio; (78 pag.)WO2016/146220; (2016); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 105-53-3, name is Diethyl malonate, A new synthetic method of this compound is introduced below., Quality Control of Diethyl malonate

(a) Isobutyldiethyl malonate Diethyl malonate is treated with an ethanol and sodium ethoxide mixture. Then iso-butyl bromide is added to form isobutyl diethyl malonate as the product of this malonic ester synthesis.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; E. R. Squibb & Sons, Inc.; US4382081; (1983); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 23676-08-6, name is Methyl 4-ethoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 23676-08-6

To a stirred suspension of CuCN (1.8 g, 20.0 mmol) in 50 mL of dry THF at -78 C under argon, a solution of 1-propenylmagnesium bromide (133.2 mmol, 265 mL of 0.5 M solution in THF) was added dropwise. The slurry was stirred for an additional 30 min and then a solution of methyl 4-ethoxybenzoate (6.0 g, 33.3 mmol) in 60 mL of dry THF was added slowly. The stirred reaction mixture was allowed to warm to room temperature overnight. The reaction wasquenched with ice cold saturated aqueous NaH2PO4 (100 mL) and the mixture was extracted with ether (4 × 100 mL). The combined ether extracts were washed with brine (2 × 100 mL), dried (MgSO4), filtered, and evaporated to dryness. The crude homoallylic ketone was purified by silica gel flash chromatography using a gradient of ethyl acetate in hexane as the eluent to give 8 (7.4 g, 95%) as a colorless oil.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 23676-08-6.

Reference:
Article; Mandal, Pijus K.; Freiter, Eric M.; Bagsby, Allison L.; Robertson, Fredika M.; McMurray, John S.; Bioorganic and Medicinal Chemistry Letters; vol. 21; 20; (2011); p. 6071 – 6073;,
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These common heterocyclic compound, 32122-09-1, name is Ethyl 2-(benzyloxy)acetate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Safety of Ethyl 2-(benzyloxy)acetate

Preparation of intermediate G-1. TiCI4, Bu3N,1 -methylimidazoleA-1 G-1To a stirred solution of A-1 (60 g, 309 mmol, 1 eq) and 1 -methylimidazole (30.4 g, 370 mmol, 1 .2 eq) in CH2CI2 (1 L) was added acetyl chloride (24.3 g, 309 mmol, 1 eq) at -45 C under N2. After stirring for 20 min, TiCI4 (210 g, 1 .08 mol, 3.5 eq) and tributylamine (230 g, 1 .24 mol, 4 eq) were added to the mixture at -45C under N2, and continues to stir for 50 minutes at -45C under N2. After completion, water and ethyl acetate were added. The organic layer was separated and the aqueous layer was extracted with ethyl acetate twice. The organic layer was washed with brine and dried over sodium sulfate. The solids were removed by filtration and the solvents of the filtrate were removed under reduced pressure. The crude was purified via silica column chromatography using a heptane to ethyl acetate gradient to afford a pale yellow oil, G-1. 1H NMR (400 MHz, CHLOROFORM-cf) delta ppm 1 .30 (t, J=7.2 Hz, 3 H), 2.28 (s, 3 H), 4.27 (q, J=7.2 Hz, 2 H), 4.41 (s, 1 H), 4.58 (d, J=1 1 .8 Hz, 1 H), 4.75 (d, J=1 1 .8 Hz, 1 H), 7.32 – 7.43 (m, 5 H)

The synthetic route of Ethyl 2-(benzyloxy)acetate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN R&D IRELAND; MC GOWAN, David; RABOISSON, Pierre Jean-Marie Bernard; EMBRECHTS, Werner; JONCKERS, Tim, Hugo, Maria; LAST, Stefaan, Julien; PIETERS, Serge, Maria, Aloysius; VLACH, Jaromir; WO2012/136834; (2012); A1;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 42726-73-8, name is tert-Butyl methyl malonate, A new synthetic method of this compound is introduced below., Product Details of 42726-73-8

Examples 1-9 demonstrate the ability to achieve consistent enantiomeric excess in the malonate/nitrostyrene reaction and that the absolute configuration of the product depends only on allosteric consequences of the oxidation state (and thus the propeller helicity of the ligand) and not on counter ion, solvent, concentration, loading, or base. The ability of Delta/Lambda-1 to catalyze the Michael addition of other nitrostyrenes and dimalonate esters was evaluated. All reactions were carried out using the indicated dimalonate ester (0.67 mmol, 2 equiv), the indicated nitrostyrene (0.34 mmol, 1 equiv), and NEt3 (10 mol percent) in MeCN (1 mL) with 5 mol percent catalyst Delta-1 or Lambda-1) at room temperature for 24 hours. The results are shown in Tables 5 and 6 below.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; NEW YORK UNIVERSITY; Canary, James; Mortezaei, Shahab; US2015/112066; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 924-99-2, category: esters-buliding-blocks

A mixture of 2,4-dichloro-5-fluoro-3-nitrobenzoic acid (10.2 g, 40 mmol) and thionyl chloride (19.0 g, 160 mmol) in dry benzene (120 ml) was refluxed for 3 – 4 h under anhydrous conditions. The solvent and excess thionyl chloride were then distilled off under reduced pressure, and dry benzene (20 ml) was then introduced into the reaction vessel and re-distilled so as to remove traces of thionyl chloride. The resulting 2,4-dichloro-5-fluoro-3-nitrobenzoyl chloride, formed as thick oil, was used as such for the next step without further purification. To a stirred and cooled (5-10 C) solution of ethyl 3-(N,N-dimethylamino)acrylate (6.3 g, 44 mmol) and triethylamine (8.1 g, 80 mmol) in dry benzene (50 ml) was added dropwise a solution of the crude acid chloride (prepared above) in dry benzene (25 ml). The resulting mixture was refluxed for 2 h, then cooled to rt and washed with water (2 x 30 ml). The organic layer was separated, dried (anhydrous MgSO4) and the solvent benzene was then evaporated to dryness under reduced pressure. The residual product was soaked in methanol (10 ml) whereby the title compound 5 was produced as yellowish powder which was collected by suction filtration and dried. Yield = 13.8 g (91%). IR (KBr): v 3074, 3037, 2988, 2928, 2873, 1689, 1619, 1554, 1454, 1397, 1375, 1344, 1321, 1278, 1206, 1177, 1129, 1030 cm-1; 1H NMR (300 MHz, CDCl3): delta 0.95 (t, J = 7.1 Hz, 3H, CH3), 2.97 (s, 3H) and 3.37 (s, 3H) [N (CH3)2], 3.94 (q, J = 7.1 Hz, 2H, CH2Me), 7.27 (d, 3JH-F = 8.2 Hz, 1H, H-6), 7.91 (br s, 1 H, N-C(3″)-H); 13C NMR (75 MHz, CDCl3): delta 13.8 (CH3CH2), 43.3, 48.4 [N (CH3)2], 60.2 (CH2Me), 100.9 (C-2″), 114.5 (d, 2JC-F = 23.3 Hz, C-4), 116.9 (d, 2JC-F = 23.1 Hz, C-6), 118.2 (d, 3JC-F = 4.5 Hz, C-1), 144.2 (d, 3JC-F = 6 Hz, C-3), 148.8 (br d, 4JC-F = 1.3 Hz, C-2), 156.6 (d, 1JC-F = 254 Hz, C-5), 160.5 (N-C-3″), 166.5 (CO2Et), 185.1 (C = O).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Ethyl 3-(dimethylamino)acrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Universitaet Duisburg-Essen; EP2128160; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 685-88-1, name is Diethyl fluoromalonate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H11FO4

To a solution of diethyl 2- fluoromalonate (5.00 g, 28.1 mmol) in EtOH (100 mL) was added LiOH H20 (2.70 g, 64.3 mmol) at 25 C. The mixture was heated to 50 C for 16 hours. The mixture was filtered to collect solid. The filtrate was concentrated to dryness to get oil. The oil and the solid were dissolved in H20 (30 mL) and MTBE (100 mL), the mixture was acidified by adding cone. HC1 to pH 1, the aqueous layer was extracted with MTBE (30 mL x2), the combined organic layers were dried over Na2S04, filtered and concentrated to give 2-fluoromalonic acid (3.00 g, yield 88%) as a solid.

According to the analysis of related databases, 685-88-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N30 PHARMACEUTICALS, LLC; SUN, Xicheng; QIU, Jian; STOUT, Adam; WO2012/83165; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics