Category: 42726-73-8

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., category: esters-buliding-blocks

9.91 Gram (95percent, 56.9 mmol) of tert-butyl methyl malonate was dissolved in 120 mL of tetrahydrofuran (THF), and the resulting solution was added dropwise to a suspension containing 2.28 g (60 wtpercent, 56.9 mmol) of sodium hydride (NaH) and 120 mL of THF at 0¡ãC over 0.5 hours, followed by stirring for 0.5 hours. Thereafter, a solution containing 8.08 g (56.9 mmol) of methyl iodide (Mel) and 20 mL of THF was added dropwise over 0.5 hours, and the resulting mixture was stirred at 0¡ãC for 0.5 hours and further stirred at 25¡ãC for 5 hours. After adding 200 mL of ethyl acetate, the organic layer was washed, in order, twice with saturated brine and twice with water, and dried over sodium sulfate, and the solvent was concentrated to obtain 13.0 g of 1-tert-butyl 3-methyl 2-methylmalonate as a colorless transparent oil. Subsequently, 45.9 g of an aqueous formalin solution was added to 13.0 g of the oil, and resulting mixture was cooled to 0¡ãC. Furthermore, 7.81 g of potassium carbonate was added, and the mixture was stirred at 0¡ãC for 1 hour and further stirred at 25¡ãC for 3 hours. After adding 200 mL of ethyl acetate, the organic layer was washed, in order, three times with an aqueous saturated sodium hydrogensulfite solution and twice with water, and dried over sodium sulfate. The solvent was concentrated, and the residue was dissolved in 50 mL of pyridine. The resulting solution was cooled to 0¡ãC, and 21.7 g of p-toluenesulfonyl chloride was added thereto. The obtained mixture was stirred at 0¡ãC for 2 hours and then stirred at 60¡ãC for 4 hours. After adding 200 mL of ethyl acetate, the organic layer was washed, in order, three times with an aqueous saturated ammonium chloride solution and twice with water, and dried over sodium sulfate. The residue was purified by column chromatography (SiO2, hexane/ethyl acetate=4/1) to obtain 15.8 g of the objective Compound (I-31) as a colorless transparent oil. 1H-NMR (400 MHz, CDCl3) delta 1.40 (s, 9H), 1.43 (s, 3H), 2.45 (s, 3H), 3.67 (s, 3H), 4.30 (s, 2H), 7.36 (d, 2H), 7.77 (d, 2H).

The synthetic route of 42726-73-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fujifilm Corporation; EP2177506; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 42726-73-8, name is tert-Butyl methyl malonate, 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. Formula: C8H14O4

EXAMPLE 125 Diethyl 2,2-Difluoroglutarate (b) Diethyl 2-ketoglutarate (a, 10.06 g, 49.74 mmol), methylene chloride (150 ml), and water (0.5 ml) were combined in a stainless steel bomb under N2 and cooled to -78. Sulfur tetrafluoride (~90 g, 833 mmol) was condensed in a polypropylene bottle at -78 and added to the reaction mixture. The bomb was sealed, then allowed to come to room temperature. After a total of 20 hrs, the bomb was vented through aqueous sodium hydroxide. The reaction mixture was worked up with methylene chloride, washing with aqueous sodium bicarbonate and brine. It yielded 11.38 g of crude yellow oil containing a white solid material. The white solid was filtered off and the oil distilled under reduced pressure through a Vigreux column. (bp 82-95, 5 mm). Total yield 6.27 g (57%) of the title compound as a light yellow oil. Silica gel tlc: Rf 0.47 in EtOAc:Hexane 1:3,

The synthetic route of tert-Butyl methyl malonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The University of Chicago; US4324730; (1982); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

42726-73-8, name is tert-Butyl methyl malonate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 42726-73-8

Tert-butyl methyl malonate (2.64 g, 15.14 mmol) was dissolved in THF (50 mL). Sodium hydride (0.605 g, 15.14 mmol) was added portion-wise at 0 ¡ãC and the reaction mixture was allowed to stir for 15 mm at room temperature. 2-chloro-5-nitropyridine (2.012.61 mmol) dissolved in 10 mL of THF was then added to the mixture and the mixture was allowed to stir for 4 hours at room temperature before being quenched withsaturated aqueous ammonium chloride and extracted with EtOAc (3x). The combined organic layer was washed with brine, dried with sodium sulfate, filtered and concentrated. The resulting residue was dissolved in 30 mL of 2:1 DCMITFA and stirred for 1.5 hours. The reaction mixture was then diluted with 1.5 M potassium phosphate solution and extracted with EtOAc (3x). The combined organic layer was washed with brine, driedwith sodium sulfate, filtered and concentrated. The resulting residue was dissolved in methylene chloride before being charged to an 80 g silica gel cartridge which was eluted with a 30 mm gradient from 0-100percent EtOAc in hexane. Fractions containing the desired product were concentrated to yield Intermediate I-109A (1.06 g, 5.40 mmol, 42.8 percent yield), as a yellow oil. LC-MS: Method H, MS (ESI) m/z: 197.0 (M+H). ?H NMR(400MHz, CDC13) 9.41 (d, J=2.6 Hz, 1H), 8.49 (dd, J8.6, 2.6 Hz, 1H), 7.56 (d, J8.6 Hz, 1H), 4.02 (s, 2H), 3.78 (s, 3H).

Statistics shows that 42726-73-8 is playing an increasingly important role. we look forward to future research findings about tert-Butyl methyl malonate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; BATES, J. Alex; HALPERN, Oz Scott; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (1137 pag.)WO2018/13774; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 42726-73-8, name is tert-Butyl methyl malonate, molecular formula is C8H14O4, 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. 42726-73-8

Example 2; Preparation of Compound 2; Compound 1 (7 g), tert-butyl methyl malonate (6 g), 0.5 ml of piperidine and 0.3 ml of acetic acid are heated under reflux for three hours in 100 ml of methanol. After cooling to room temperature, the mixture is filtered and the filtrate is concentrated. The concentrated filtrated is poured into water, and resulted precipitate is filtered off with suction to collect the solid that is air-dried. The crude product is further purified with silica gel chromatography to yield the desired Compound 2.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl methyl malonate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AAT Bioquest, Inc.; US8318953; (2012); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 42726-73-8, name is tert-Butyl methyl malonate, 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 42726-73-8, 42726-73-8

tert-Butyl methyl malonate (3.9 mL, 23 mmol), potassium carbonate (7.9 g, 57.5 mmol) and dibromoethane (2.57 mL, 29.9 mmol) were combined in DMF (75 mL) and the resulting reaction mixture was stirred at room temperature overnight. The mixture was poured onto water (500 mL) and extracted with ether (3 X). The combined ethereal layers were washed with water, then washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by flash chromatography (0-5percent EtOAc/ hexane) provided l-(tert-butyl) 1-methyl cyclopropane-l,l-dicarboxylate (2.35 g, 51percent yield). Combined with another batch afforded the desired product (4.28 g). 1H NMR (300 MHz, Chloroform-d) delta 3.75 (s, 3H), 1.47 (s, 9H), 1.38 (s, 4H).

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, tert-Butyl methyl malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF HAWAII; TURKSON, James; YUE, Peibin; TIUS, Marcus; BROTHERTON-PLEISS, Christine; LOPEZ TAPIA, Francisco, Javier; (420 pag.)WO2018/136935; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

42726-73-8,Some common heterocyclic compound, 42726-73-8, name is tert-Butyl methyl malonate, molecular formula is C8H14O4, 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.

To a round bottom flask was charged with S11 (10.0 g, 0.056 mol, 1.0 equiv.), tert-butyl methylmalonate (12.3 ml, 0.074 mol, 1.3 equiv.), (S)-2-(diphenyl((trimethylsilyl)oxy)methyl)pyrrolidi-ne (3.7 g, 0.011 mol, 0.2 equiv.), and 100 mL of EtOH. The reaction mixture was stirred atroom temperature for 16 h and was then concentrated in vacuo. Purification of the crudeproduct by flash chromatography on silica gel (petroleum ether:EtOAc, 5:1 v/v) afforded S2as a pair of diastereoisomers (15.1 g, 76percent), both as yellow oil.S2-upper: TLC (petroleum ether:EtOAc, 5:1 v/v): Rf = 0.30; 1H NMR (400 MHz, CDCl3): delta 9.68 (s, 1H), 7.81 (d,J = 8.8 Hz, 1H), 7.55 (t, J = 7.2 Hz, 1H), 7.46 (d, J = 7.6 Hz, 1H), 7.39 (t, J = 8.4 Hz, 1H), 4.56 ? 4.50 (m, 1H),3.83 (d, J = 9.2 Hz, 1H), 3.57 (s, 3H), 3.12 ? 2.97 (m, 2H), 1.43 (s, 9H); 13C NMR (100 MHz, CDCl3): delta 199.6,167.9, 166.5, 150.3, 134.8, 132.8, 129.3, 128.2, 124.7, 83.2, 57.2, 52.6, 46.6, 33.7, 27.8, 27.8, 27.8; IR (neat): vmax= 1727, 1355, 845, 749 cm-1; HRMS (m/z): [M + Na] + calcd. for C17H21NNaO7, 374.1210; found 374.1210; [alpha]D25= +63.4 (c 0.20, MeOH).S2-lower: TLC (petroleum ether:EtOAc, 5:1 v/v): Rf = 0.26; 1H NMR (400 MHz, CDCl3): delta 9.68 (s, 1H), 7.82 (d,J = 8.4 Hz, 1H), 7.55 (t, J = 8 Hz, 1H), 7.46 (d, J = 7.6 Hz, 1H), 7.38 (t, J = 7.6 Hz, 1H), 4.53 ? 4.47 (m, 1H), 3.87(d, J = 9.6 Hz, 1H), 3.73 (s, 3H), 3.08 ? 2.94 (m, 2H), 1.20 (s, 9H); 13C NMR (100MHz, CDCl3): delta 199.6, 168.4,165.9, 150.2, 135.0, 132.9, 129.5, 128.2, 124.7, 82.8, 57.1, 52.7, 47.3, 34.1, 27.4, 27.4, 27.4; IR (neat): vmax =1727, 1529, 844, 787 cm-1; HRMS (m/z): [M + Na] + calcd. for C17H21NNaO7 374.1210; found 374.1210; [alpha]D25 =+32.5 (c 0.30, MeOH).

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

Reference:
Article; Wang, Xiaobei; Xia, Dongliang; Qin, Wenfang; Zhou, Ruijie; Zhou, Xiaohan; Zhou, Qilong; Liu, Wentao; Dai, Xiang; Wang, Huijing; Wang, Shuqing; Tan, Ling; Zhang, Dan; Song, Hao; Liu, Xiao-Yu; Qin, Yong; Chem; vol. 2; 6; (2017); p. 803 – 816;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

42726-73-8, A common compound: 42726-73-8, name is tert-Butyl methyl malonate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Example 13 L3-(7-Methoxy-indol-1- lY )-3-pyridin-3- T(at)l-propyll-methyl-aznine The synthetic procedure of Example 12 is outlined in Scheme L below. SCHEME L Step; 2-Pyridin-3-ylmethylene-malonic acid tert-butyl ester methyl ester A mixture of pyridine-3-carboxaldehyde (2.72 g), propanedioic acid, 1,1-dimethylethyl methyl ester (4.42 g), piperidine (0.173 g) and benzoic acid (0.155 g) in benzene (100 ml) was heated at reflux with removal of water to a Dean-Stark trap for 12 hours. The cooled mixture was washed with bicarbonate solution, concentrated under vacuum and the residue was purified by column chromatography, eluting with ethyl acetate – hexane (3 : 7) to afford racemic 2-pyridin-3-ylmethylene-malonic acid tert-butyl ester methyl ester as an oil (3.21 g).

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, tert-Butyl methyl malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F.HOFFMANN-LA ROCHE AG; WO2005/118539; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

42726-73-8, Name is tert-Butyl methyl malonate, 42726-73-8, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

Potassium hydroxide (2.00 g, 36.0 mmol), tert-butyl methyl malonate (1.22 mL, 7.2 mmol) and DCM (20 mL) were added to a 100-mL flask under inert atmosphere. The mixture was stirred at room temperature until the solution became white then PhI(OAc)2 (1.93 g, 6.0 mmol) was added and stirred at room temperature for 2 hours. The solution was filtered through a cotton plug and washed with small portions of DCM. The solvent was removed under reduced pressure and the remaining oil was placed under high vacuum for 2 hours. The oil crystallized and the resulting solid was used without further purification. 1.038 g (46percent); off-white solid; m.p. 95-97¡ãC (dec.); 1H NMR (CDCl3; 600 MHz): delta 1.45 (s, 9H), 3.77 (s, 3H), 7.40-7.43 (m, 2H), 7.52-7.54 (m, 1H), 7.71-7.73 (m, 2H); 13C NMR (CDCl3; 150 MHz): delta 28.6, 52.5, 80.1, 114.5, 127.5, 130.3, 131.3, 131.5, 163.9, 164.4; HRMS: Calculated for C14H18IO4 (377.0250) [M+H]+, Found: 377.0255.

Statistics shows that tert-Butyl methyl malonate is playing an increasingly important role. we look forward to future research findings about 42726-73-8.

Reference:
Article; Stokes, Sean; Mustain, Rachel; Pickle, Lydia; Mead, Keith T.; Tetrahedron Letters; vol. 53; 30; (2012); p. 3890 – 3893;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics