Month: May 2021

Related Products of 87661-20-9, 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. 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows.

Under argon, 1.28 ml (9.15 mmol) of diisopropylamine were initally charged in 6 ml of dry THF, and the mixture was cooled to -40 C. 4.26 ml (9.15 mmol) of n-butyllithium solution (2.5 M in hexane) were slowly added dropwise, and the mixture was stirred for 30 min. The reaction solution was then cooled to -78 C., and a solution of 1.30 g (9.15 mmol) of tert-butyl cyclopropanecarboxylic acid in 2 ml of THF was added. After 4 h of stirring at -78 C., a solution of 2.00 g (8.69 mmol) of 1-(bromomethyl)-2-methyl-3-nitrobenzene in 2 ml of THF was added. Slowly, the reaction mixture was warmed to RT overnight. Ammonium chloride solution was then added carefully, and the mixture was extracted three times with ethyl acetate. The combined organic phases were washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/dichloromethane 50:1, then 5:1). This gave 0.78 g (29.3% of theory) of the title compound.1H-NMR (400 MHz, DMSO-d6): delta=7.61 (d, 1H), 7.54 (d, 1H), 7.39 (t, 1H), 2.96 (s, 2H), 2.26 (s, 3H), 1.26 (s, 9H), 1.20 (q, 2H), 0.79 (q, 2H).

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

Reference:
Patent; BAYER SCHERING PHARMA AKTIEGESELLSCHAFT; US2011/34450; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 87661-20-9, A common heterocyclic compound, 87661-20-9, name is tert-Butyl cyclopropanecarboxylate, molecular formula is C8H14O2, 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 a solution of LDA in THF (40 mL of a 0.8 M solution; 33.2 mmol) at -78 C. was added tert-butyl cyclopropane carboxylate (3.78 g, 26.6 mmol) dropwise over 10 min. The solution was stirred at -78 C. for 2 h, after which 1-bromopropane (4.84 mL, 53.2 mmol) was added dropwise over 20 min at -78. The reaction was allowed to slowly warm to RT and stirred overnight at RT, then was quenched with sat’d aq. NH4Cl and extracted with EtOAc (2*). The combined organic extracts were washed with brine, dried (MgSO4), and concentrated in vacuo. The residue was distilled under reduced pressure (20 torr, BP=95 C.) to give the title compound (2.99 g, 61% yield) as an oil. 1H NMR (500 MHz, CDCl3) delta 1.48 (m, 4H), 1.45 (s, 9H), 1.12 (m, 2H), 0.92 (m, 3H), 0.61 (m, 2H).

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; BRISTOL-MYERS SQUIBB COMPANY; SHI, YAN; Cheng, Peter Tai Wah; Wang, Ying; Shi, Jun; Tao, Shiwei; Li, Jun; Kennedy, Lawrence J.; Kaltenbach, III, Robert F.; Zhang, Hao; Corte, James R.; US2019/185446; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 4911-54-0, name is Ethyl 4-methylpent-4-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. name: Ethyl 4-methylpent-4-enoate

EXAMPLE 13 The reaction is carried out as described in Example 8 but using catalyst 4a (7.6 mg, 0.01%) in THF (5 ml) and KOMe (0.63 g, 9 mmol) in ethyl 4-methylpent-4-enoate 11 (12.9 g, 91 mmol) and THF (58 ml). Standard work-up gave a slightly yellow crude oil (5.6 g, 61%) which contained 4-methyl pent-4-en-1-ol 12 of 100% purity according to GC. The analytical data of 4-methylpent-4-en-1-ol 12 were identical with the ones obtained from commercial samples of this compound.

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

Reference:
Patent; Geisser, Roger Wilhelm; Goeke, Andreas; Schroeder, Fridtjof; US2015/152029; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 19063-56-0, The chemical industry reduces the impact on the environment during synthesis 19063-56-0, name is 7-Bromo-2H-chromen-2-one, I believe this compound will play a more active role in future production and life.

General procedure: A 10 mL vial equipped with a small magnetic stirring bar wascharged with the appropriate bromo O-hetarene (1.0 equiv, 100mg), Pd(OAc)2 (5 mol%), and CuI (1.0 equiv). Anhyd DMF (1 mL)and the appropriate 1,3-azole (2.0 equiv) were added, and thevessel was purged with N2 and sealed with a PEEK snap cap. Themixture was stirred for 5 min at r.t. before the vessel was placedin the microwave reactor and the mixture was heated to 140 Cwith stirring for the appropriate time (usually 1 h). The solutionwas then cooled to r.t., diluted with EtOAc (15 mL), washed withsat. aq NH4Cl (2 × 15 mL) and dilute aq Na2S2O3 (10 mL). Theaqueous phases were extracted with EtOAc (2 × 10 mL), and theorganic phases were combined and washed with sat. aq NH4Cl(10 mL) and brine. Some H2O was added if any solids precipitatedduring the extraction. The combined organic phases weredried (MgSO4), filtered, and concentrated. The residue was purifiedby column chromatography (silica gel).

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, 7-Bromo-2H-chromen-2-one, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Sipos, Zoltan; Konya, Krisztina; Synlett; vol. 29; 18; (2018); p. 2412 – 2416;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 264276-14-4,Some common heterocyclic compound, 264276-14-4, name is Dimethyl 2,6-dichloroterephthalate, molecular formula is C10H8Cl2O4, 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 stirred solution of dimethyl 2,6-dichlorobenzene-1,4-dicarboxylate (2 g, 7.6 mmol, Step b) in tetrahydrofuran and water (1:1, 20 mL), sodium hydroxide (304 mg, 7.6 mmol) was added and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated under vacuum and the residue was neutralized using cold hydrochloric acid (1N). The precipitated solid was filtered under suction, washed with hexane and dried to afford 3,5-dichloro-4-(methoxycarbonyl)benzoic acid as an white solid (1.5 g, 85%). 1H NMR (400 MHz, DMSO-d6): delta 7.93 (s, 2H), 3.94 (s, 3H). MS: 247.6 (M-2), 249.6 (M).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl 2,6-dichloroterephthalate, its application will become more common.

Reference:
Patent; Daiichi Sankyo Company, Limited; Verma, Ashwani Kumar; Nagaswamy, Kumaragurubaran; Sharma, Lalima; Ghosh, Soma; Kale, Balkrishna Ramchandra; Mondal, Aniruddha; Srivastava, Punit Kumar; Dastidar, Sunanda Ghosh; Momin, Rijwan Jaffer; Wagh, Pradip Balu; Pansare, Sonali Nanasaheb; Markad, Pramod Raosaheb; Khairnar, Yogesh Balasaheb; Miyauchi, Rie; Murata, Takeshi; Ishizaki, Masayuki; Nagamochi, Masatoshi; Iimura, Shin; US2014/155398; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 6232-12-8,Some common heterocyclic compound, 6232-12-8, name is Ethyl 4-(aminomethyl)benzoate hydrochloride, molecular formula is C10H14ClNO2, 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.

4-Chloro-naphthalimidyl-methylbencoic acid- ethylester (2):; 20.0 g (93.2 mM) 4- aminomethylbencoic acid-ethylester hydrochloride , 21.68 g (93.2 mM) 4-Chloro-l,8-naphthalic anhydride and 19.78 g triethylamine (195.5 mM) in 400 ml DMF were heated to 900C and stirred overnight.[0044] After cooling to room temperature, 100 ml H2O were added to precipitate the desired product.[0045] The 4-Chloro-naphthalimidyl-methylbencoic acid-ethylester was recrystallized from EtOH. Yield: 15.8 g.[0046] The HPLC (Vydac 10-90- 15) shows a single peak at t = 14.04 and the mass peak MH+ = 394.8 ( M = 393.82) was found in the Matrix Assisted Laser Desorption/Ionization Time-of- Flight (MALDI-TOF) mass spectrum.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4-(aminomethyl)benzoate hydrochloride, its application will become more common.

Reference:
Patent; ROCHE DIAGNOSTICS GMBH; F. HOFFMANN-LA ROCHE AG; WO2006/58778; (2006); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 41191-92-8, name is Ethyl 3-amino-4-methylbenzoate, 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 3-amino-4-methylbenzoate

EXAMPLE 14 Ethyl 3-[[(5,6-dihydro-2-methyl-1,4-oxathiin-3-yl) carbonyl]amino]-4-methylbenzoate (Compound 14) Thionyl chloride (4.5 g, 0.038 mole) was added to a stirred mixture of 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxylic acid (6.0 g, 0.037 mole) and methylene chloride (100 ml. The mixture was warmed to 30-35 C. for 3 hours, then evaporated under reduced pressure. The residue, crude 5,6-dihydro-2-methyl-1,4-oxathiin-3-carbonyl chloride, was dissolved in methylene chloride (100 ml), and the ice-chilled solution treated dropwise with a solution of ethyl 3-amino-4-methylbenzoate (6.7 g, 0.037 mole) and triethylamine (4.0 g, 0.040 mole) in methylene chloride (100 ml). The reaction mixture was stirred overnight at room temperature and then worked up by washing in sequence with water, dilute hydrochloric acid, water, 2% sodium hydroxide and water. Evaporation of the solvent gave an oil, which solidified. After recrystallization from ethanol (30 ml), the product (7.1 g, 59% yield) melted at 105-107 C. Analysis: Calc.: C 59.79, H 5.96, N 4.36, Found: C 59.87, H 5.73, N 4.52 NMR: (CDCl3): 1.35 (3H,t), 2.25 (3H,s), 2.3 (3H,s) 2.3 (3H,s), 3.0 (2H,m), 4.15-4.55 (4H,m), 7.1-7.3 (1H,m), 7.55-7.95 (2H,m), 8.45 (1H,d)

The synthetic route of Ethyl 3-amino-4-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Uniroyal Chemical Company, Inc.; Uniroyal Chemical Ltd./Ltee; US5268389; (1993); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 103-09-3, 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. 103-09-3 name is 2-Ethylhexyl 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.

Reduce the temperature to 20-25 C, add 39.5kg (0.73kmol) of sodium methoxide solid, start stirring, control the temperature of the kettle at 20-25 C, and add 93.8kg (0.69kmol) of p-methoxybenzaldehyde dropwise within 30min. the temperature was raised to 110 C until the GC content of p-methoxybenzaldehyde was less than 0.25%. It takes about 1h.After the reaction is completed, water is added to the reaction system, stirred, left to stand, and separated into layers.An aqueous layer and an organic layer were obtained. Washing the organic layer to separate the aqueous layer,Obtain a washed organic layer, rectifying the organic layer, the yield of isooctyl p-methoxycinnamate was 183.0 kg (0.63 kmol), and the yield was 91.5%.

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

Reference:
Patent; Anhui Shengnuobei Chemical Technology Co., Ltd.; Liu Qifa; Wang Rong; Yang Jian; Wang Zhongxiao; Li Juan; (12 pag.)CN110540505; (2019); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 54810-63-8, name is Methyl 2-chloro-5-methoxybenzoate, 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 54810-63-8, Recommanded Product: Methyl 2-chloro-5-methoxybenzoate

Methyl (2-chloro-5-methoxy)benzoate (18) (1.19 g, 6.47 mmol) was stirred vigorously in neat aqueous ammonia (28%, 7.8 mL) at room temperature. After 24 h, the resulting mixture was treated with chloroform and the separated organic phase washed with aqueous hydrochloric acid (5 M, 55 mL), water (40 mL), brine (40 mL) then dried (MgSO4), filtered and concentrated under reduced pressure to give 19 as a white powder (0.93 g, 78% yield). m.p. 125.3-126.9 C; IR (ZnSe): 3372, 3178, 1650, 1480, 1461, 1446, 1239, 1028, 821 cm-1; 1H NMR (300 MHz, MeOD): delta 7.34 (1H, d, J = 8.8 Hz), 7.05 (1H, d, J = 2.9 Hz), 7.00 (1H, dd, J = 2.9 and 8.8 Hz), 3.81 (3H, s) ppm; 13C NMR (75 MHz, MeOD): delta 172.1, 159.8, 137.9, 132.0, 122.8, 117.9, 115.2, 56.2 ppm; LRMS (GC-MS): 185 ([M], 60%), 169 ([M-NH2], 100%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-chloro-5-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Article; Callis, Timothy B.; Reekie, Tristan A.; O’Brien-Brown, James; Wong, Erick C.N.; Werry, Eryn L.; Elias, Nabiha; Jorgensen, William T.; Tsanaktsidis, John; Rendina, Louis M.; Kassiou, Michael; Tetrahedron; vol. 74; 12; (2018); p. 1207 – 1219;,
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. 85920-63-4, name is 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

In an adaptation of general procedure 29b: Acetyl meldrum’s acid (27.4 g, 147 mmol, 3 eq.) and 2-[2-(2-fluoro-6-trifluoromethyl-phenyl)-ethyl]-4,5-dihydro-oxazole-4-carboxyl i c aci d methyl ester (intermediate E.8) (15.6 g, 49.0 mmol) in toluene (300 mL) were heated to reflux for 20 min. Then trifluoro acetic acid (18.9 mL, 27.9 g, 245 mmol, 5 eq.) was added and reflux was continued for 1 hour. The reaction mixture was partitioned between water and ethyl acetate. After phase separation, extraction of the aqueous layer with ethyl acetate, washing of the combined organic layers with brine and evaporation of the solvent flash chromatography yielded the desired title compound (yield: 4.7 g)1H-NMR (methanol-d4, 300 MHz): 3.77 (s, 3H); 3.99 (s, 2H); 4.64 (dd, 1 H); 4.75 (t, 1 H); 5.23 (dd, 1 H); 5.96 (s, 1 H); 7.30 (m, 1 H); 7.38 – 7.47 (m, 1 H); 7.48 – 7.55 (m, 1 H).MS (ESI+): [M + H]+ = 386

According to the analysis of related databases, 85920-63-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; HUeBNER, Jan; WEGSCHEID-GERLACH, Christof; PANKNIN, Olaf; RING, Sven; BAeURLE, Stefan; HUWE, Christoph; NOWAK, Katrin; NUBBEMEYER, Reinhard; MUHN, Hans-Peter; WO2011/76687; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics