Tag: M.W=100-200

Reference of 141-12-8,Some common heterocyclic compound, 141-12-8, name is (Z)-3,7-Dimethylocta-2,6-dien-1-yl acetate, molecular formula is C12H20O2, 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.

General procedure: To a solution of the geranyl derivative (1.0 equiv) in acetonitrile(0.05 M) at 0 C, lithium bromide (2.0-2.4 equiv),4 A molecular sieves (1.0 mass equiv) and DIB (1.2-1.4 equiv) were added. After stirring for 5 min, the reaction mixture wasdiluted with EtOAc, filtered over alumina (EtOAc) and concentratedunder reduced pressure before purification by flash chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (Z)-3,7-Dimethylocta-2,6-dien-1-yl acetate, its application will become more common.

Reference:
Article; Peilleron, Laure; Grayfer, Tatyana D.; Dubois, Joelle; Dodd, Robert H.; Cariou, Kevin; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 1103 – 1111;,
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Electric Literature of 27798-60-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 27798-60-3 as follows.

Example 7a 3-(2,4-Dichloro-pyrimidin-5-yl)-2-(2-methoxy-phenyl)-propionic acid methyl ester To a solution of N-isopropylcyclohexylamine (1.44 g, 10.0 mmol) (Aldrich) in dry tetrahydrofuran (20 ML) was added n-butyllithium (2.5 M in hexanes, 4.0 ML, 10.0 mmol) (Aldrich) at -78 C. under argon.After 30 minutes, a solution of 2-methoxyphenylacetic acid methyl ester (1.8 g, 10.0 mmol) (TCI-US) in tetrahydrofuran (5 ML) was added by injection via a syringe and the reaction mixture was stirred at -78 C. for another 30 minutes.To the reaction mixture was added a solution of 2,4-dichloro-5-iodomethyl-pyrimidine (1.45 g, 5.0 mmol) (from Example 1c supra) in tetrahydrofuran (5 ML) at -78 C. and the reaction mixture was stirred at the same temperature for 1 hour then slowly allowed to warm up to -30 C. and stirred for 10 minutes.The reaction mixture was diluted with ethyl acetate (100 ML) and successively washed with saturated aqueous ammonium chloride solution (100 ML), water (50 ML) and brine (50 ML), dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo.The residue was purified by flash column chromatography to give 3-(2,4-dichloro-pyrimidin-5-yl)-2-(2-methoxy-phenyl)-propionic acid methyl ester as a yellow oil. (Yield 1.40 g, 82.3%).

According to the analysis of related databases, 27798-60-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Liu, Jin-Jun; Luk, Kin-Chun; US2004/122029; (2004); A1;,
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14062-18-1, name is Ethyl 2-(4-methoxyphenyl)acetate, 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. Application In Synthesis of Ethyl 2-(4-methoxyphenyl)acetate

1 g of 4-methanesulfony benzoicacid, 970 mg of 4-methoxyphenylacetic acid ethyl ester, and 950 mg of carbonyldiimidazole were dissoved in 15 ml of dimethylformamide and 230 mg of sodium hydride were added dropwise to the solution and the mixture was reacted in room temperature for 12 hours. Afterwards, water was added to diute the resultant, followed by extraction with ethyl acetate. The obtained organic layer was dried over anhydrous magnesium sulfate to give 1.5 g of the title compound as a light yellow liquid(yield 83%).

The synthetic route of 14062-18-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Cho, Il Hwan; Noh, Ji Young; Park, Sang Wook; Ryu, Hyung Chul; Lim, Jee Woong; Kim, Jong Hoon; Chae, Myeong Yun; Kim, Dal Hyun; Jung, Sung Hak; Park, Hyun Jung; Kim, Young Hoon; Min, In Ki; US2004/2532; (2004); A1;,
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Related Products of 37746-78-4, These common heterocyclic compound, 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, 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.

To the suspension of potassium phthalimide (4.5 mmol) in dry DMF (4 mL) was added a solution of (E)-alkyl -bromobut-2-enoate in dry DMF (3 mL). The reaction was run at room temperature overnight. After the reaction was omplete, the reaction mixture was poured into water and extracted with ether and concentrated in vacuum to leave a hite solid. The residue can be easily purified by flash chromatography (petroleum/ethyl acetate, 4:1), to give the desired compounds 1.

The synthetic route of 37746-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Han, Fuzhong; Chen, Jun; Zhang, Xiangyang; Liu, Jibing; Cun, Linfeng; Zhu, Jin; Deng, Jingen; Liao, Jian; Tetrahedron Letters; vol. 52; 7; (2011); p. 830 – 833;,
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Synthetic Route of 927-68-4, 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. 927-68-4 name is 2-Bromoethyl acetate, 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.

To a solution of 2-methoxy-5-nitro-phenol (1.0 g, 5.9 MMOL) in dry DMF (20 ML), under N2, was added K2CO3 (1. 1 eq. , 0.9 g) and 2-BROMOETHYL acetate (1.1 eq, 0.714 ML). After heating to 60 C for 4 hours, a saturated solution of NH4CI was added and the mixture was extracted with DICHLOROMETHANE. The organic phase was washed with water, dried over NA2SO4, filtered and then concentrated in vacuo, to give 1.5 g of the crude intermediate compound. This was dissolved in dry methanol (34 ML) and MeONa (31 mg, 0.58 MMOL) was added. After 1H an excess of Amberlite IR120 (H+ FORM) was added, the solution was filtered and concentrated in vacuo. The residue was dissolved in DICHLOROMETHANE and washed with NAOH 0.1 N and water. The organic phase was dried over NA2SO4, filtered and then concentrated in vacuo, to give 1.1 g of the title compound as a pale yellow solid (m. p. 115 C). NMR ( H, CDCI3) : No. 7. 95 (dd, 1 H), 7.80 (d, 1H), 6.94 (d, 1H), 4.21 (t, 2H), 4.03 (t, 2H), 3.98 (s, 3H), 2.3 (bs, 1H). MS (M/Z) : 214 [MH] +.

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

Reference:
Patent; GLAXO GROUP LIMITED; WO2004/89897; (2004); A1;,
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Application of 46004-37-9, 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. 46004-37-9, name is Methyl 4-amino-2-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-chloro-4-aminobenzoic acid, methyl ester (13.95 g) was suspended in a mixture of water (65 ml) and concentrated hydrochloric acid (15.7 ml). After stirring at room temperature for 10 minutes, the suspension was cooled to 0 C. A solution of sodium nitrite (5.71 g) in water (37 ml) was gradually added over 20 minutes, maintaining a reaction temperature of 0 C. After stirring at 0 C. for 35 minutes, the reaction mixture was partially neutralized by the addition of solid sodium carbonate (3.16 g) to afford a cold solution of the diazonium salt.

The synthetic route of Methyl 4-amino-2-chlorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Cyanamid Company; US6831079; (2004); B1;,
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Reference of 1459-93-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1459-93-4 as follows.

Methyl isophthalate (2.00 g, 11.1 mmol) was dissolved in THF (60 mL), and a 2.0 mol/L solution of dimethylamine (11.1 ml, 22.2 mmol) in methanol, EDC hydrochloride (4.27 g, 22.2 mmol) and 1-hydroxybenzotriazole monohydrate (3.40 g, 22.2 mmol) were added thereto, followed by stirring at room temperature for 2 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate = 1:3) to afford methyl 3-(N,N-dimethylcarbamoyl)benzoate (2.30 g, 100 %).

According to the analysis of related databases, 1459-93-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KYOWA HAKKO KOGYO CO., LTD.; EP1700856; (2006); A1;,
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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. 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C9H16O3

To a solution of ethyl 4-hydroxycyclohexanecarboxylate 2 (mixture of cis and trans) (2.5 g, 14.5 mmol) and imidazole (1.97 g, 29 mmol) in anhydrous DMF (20 mL), tert-butyldimethylsilyl chloride (2.63 g, 17.5 mmol) was added. After stirring overnight, Et2O (60 mL) and 1M aqueous HCl (60 mL) were added. After extraction with Et2O, the combined organic phases were washed with 1M aqueous HCl and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to give a TBS-protected alcohol as a colorless oil (4.14 g), which was used in the next step without further purification. To a solution of the former alcohol (4.14 g, 14.5 mmol) in THF (20 mL) and methanol (12 mL), lithium hydroxide (0.7 g, 29 mmol) was added. The mixture was then stirred at 60 C for 3 h. After removal of the solvents, water and Et2O were added and the aqueous layer was extracted with diethyl ether, cooled in an ice bath then acidified to pH=1 with 1M aqueous HCl. After extraction with ethyl acetate, the organic phases were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate, 50:50) to give the title compound 3 as a mixture of cis/trans isomers (3.48 g, 100% yield) as a colorless oil; deltaH (400 MHz, CDCl3) 10.84 (2H, m, 2*COOH), 3.89 and 3.56 (2*1H, 2*bs, 2*H-4), 2.41-2.18 (2H, m, 2*H-1), 2.10-1.83 (6H, m), 1.74-1.59 (4H, m), 1.58-1.23 (6H, m), 0.88 and 0.87 (2*9H, 2*s, 2*(CH3)3CSi), 0.05 and 0.03 (2*6H, 2*s, 2*(CH3)2Si); deltaC (100 MHz; CDCl3) 181.8 (2*COOH), 70.5 and 66.7 (2*C-4), 42.0 and 41.9 (2*C-1), 34.8 (2*CH2), 32.9 (2*CH2), 27.1 (2*CH2), 23.4 (2*CH2), 26.1 and 26.0 (2*(CH3)3CSi), 18.3 and 18.2 (2*(CH3)3CSi), -4.5 and -4.7 (2*(CH3)2Si).

The synthetic route of 3618-04-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zeinyeh, Wael; Radix, Sylvie; Terreux, Raphael; Chemelle, Julie-Anne; Walchshofer, Nadia; Tetrahedron; vol. 72; 27-28; (2016); p. 4032 – 4038;,
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These common heterocyclic compound, 105-53-3, name is Diethyl 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. Recommanded Product: 105-53-3

EXAMPLE 14: PREPARATION OF 1 ,1 CYCLOPRANEDIESTER (FORMULA XVI):1 ,2-dichloroethane (400 liters), diethyl malonate (145 kg), N,N-dimethyl formamide (365 liters), and potassium carbonate (187 kg) were taken into a reactor equipped with a Dean-Stark type azeoptropic apparatus. The reaction mixture was heated to reflux followed by stirring for about 30 hours, simultaneously removing unwanted water that was collected in the Dean Stark apparatus. The reaction mixture was cooled to about 30 0C. The reaction mass was filtered and the filter washed with 510 L of 1 ,2-dichloroethane. The obtained organic layer was washed with water (4*510 L water) and distilled completely under vacuum below 6O0C to obtain a residue. The obtained residue was cooled to 35 0C and high vacuum applied. The reaction mass was heated slowly below 75C and collect the first fraction. The second fraction was collected by maintaining the temperature at 900C and the third fraction was collected by maintaining the temperature below 120C for about 5 hours to afford 18.5 kg (2nd and 3rd fractions) of the title compound. Purity by GC: 92.44%.

The synthetic route of Diethyl malonate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DR. REDDY’S LABORTORIES, LTD.; DR. REDDY’S LABORATORIES, INC.; WO2008/58118; (2008); A2;,
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Synthetic Route of 34837-84-8, 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. 34837-84-8, name is Methyl 2-(4-fluorophenyl)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

5A. Methyl 2-(4-fluorophenyl)-3-(4-(methylsulphonyl)phenyl)-3-oxopropanoate A solution of methyl 2-(4-fluorophenyl)acetate (2.35 g, 14 mmol) in THF (15 mL), at -78° C., was treated dropwise with 1 N lithium bis(trimethylsilyl)amide (14 mL, 14 mmol). After 15 minutes a suspension of 4-(methylsulphonyl)benzoyl chloride (3.3 g, 15 mmol) in THF (25 mL) was added in portions. The reaction mixture was stirred for 60 minutes at -78° C. and at 0 to 5° C. for 12 hours. The mixture was quenched with 10percent citric acid, the THF removed in vacuo, and the residue triturated with hexanes to provide the desired product as a solid (yield: 3.4 g; 69percent). MS (DCI-NH3) m/z 368 (M+H)+; 1H NMR (300 MHz, DMSO-d6) delta3.27 (s, 3H), 3.69 (s, 3H), 6.35 (s, 1H), 7.21 (m, 2H), 7.44 (m, 2H), 8.06 (d, J=9 Hz, 2H), 8.25 (d, J=9 Hz, 2H).

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, Methyl 2-(4-fluorophenyl)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Abbott Laboratories; US6472416; (2002); B1;,
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Ester – an overview | ScienceDirect Topics