Tag: M.W=100-200

Adding a certain compound to certain chemical reactions, such as: 4934-99-0, name is Methyl 3-hydroxycyclobutanecarboxylate, 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 4934-99-0, Quality Control of Methyl 3-hydroxycyclobutanecarboxylate

Methyl 3-(tert-butoxy)cyclobutane-1-carboxylate In a 30-mL round bottom flask purged and maintained with an inert atmosphere of nitrogen, methyl 3-hydroxycyclobutane-1-carboxylate (200 mg, 1.54 mmol, 1.00 equiv) and di-tert-butyl dicarbonate (771.4 mg, 3.53 mmol, 2.30 equiv) were mixed in dichloromethane (10 mL), to which was added magnesium perchlorate (34.3 mg, 0.15 mmol, 0.10 equiv) at room temperature. The resulting solution was then stirred for 16 h at 40 C. When the reaction was done, it was quenched with 10 mL water and the mixture was extracted with dichloromethane (3*10 mL). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by prep-TLC eluting with ethyl acetate in petroleum ether (50%) to afford methyl 3-(tert-butoxy)cyclobutane-1-carboxylate (200 mg, 70%) as yellow oil. MS: m/z=187.1 [M+H]+.

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 3-hydroxycyclobutanecarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck Patent GmbH; GAILLARD, Pascale; SEENISAMY, Jeyaprakashnarayanan; LIU-BUJALSKI, Lesley; CALDWELL, Richard D.; POTNICK, Justin; QIU, Hui; NEAGU, Constantin; JONES, Reinaldo; WON, Annie Cho; GOUTOPOULOS, Andreas; SHERER, Brian A.; JOHNSON, Theresa L.; GARDBERG, Anna; (234 pag.)US2016/96834; (2016); A1;,
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Application of 6627-89-0, A common heterocyclic compound, 6627-89-0, name is tert-Butyl phenyl carbonate, molecular formula is C11H14O3, 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.

EXAMPLE 2 7-t-Butyloxycarbonylaminoheptanoic Acid 7-Aminoheptanoic acid (20 g., 1.38 * 10-1 moles) was converted to the title compound using the method of Ulf Ragnarrson et al., Org. Syn., 53, 25 (1973), using tetramethylguanidine (17.3 g., 1.49 * 10-1 moles) and t-butylphenylcarbonate (30 g., 1.54 * 10-1 moles) in dimethylsulfoxide (100 ml.) for three days. The product (24 g.) had m.p. 56-58 after recrystallization from ethyl acetate-hexane-ether. Analysis for: C12 H23 NO4. Calculated: C, 58.75; H, 9.45; N, 5.71. Found: C, 59.14; H, 9.61; N, 5.86.

The synthetic route of 6627-89-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Home Products Corporation; US4133805; (1979); A;,
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Adding a certain compound to certain chemical reactions, such as: 34837-84-8, name is Methyl 2-(4-fluorophenyl)acetate, 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 34837-84-8, Safety of Methyl 2-(4-fluorophenyl)acetate

General procedure: Various methyl benzoate 8A-V (1.0 equiv) reacted with hydrazine hydrate (excess amount) in anhydrous ethanol. The reaction was stirred at 40 ¡ãC for overnight. The ethanol was removed under reduced pressure. The products were purified by recrystallization, which were washed with ethyl ether. The products were obtained as white solid.

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Reference:
Article; Kim, Bo-Kyoung; Ko, Hyojin; Jeon, Eun-Seok; Ju, Eun-Seon; Jeong, Lak Shin; Kim, Yong-Chul; European Journal of Medicinal Chemistry; vol. 120; (2016); p. 202 – 216;,
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Application of 13195-64-7, 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. 13195-64-7, name is Diisopropyl malonate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1) sodium hydride as catalyst to 830mmol, 200mmol the diisopropyl malonate 440mmol with propargyl bromide was added to 210mL of anhydrous acetonitrile ice-water bath, the reaction was stirred for 8 hours, the product was washed with water, added with ethyl acetate, spin-dry under reduced pressure to give a tan solid product, compound 1;

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, Diisopropyl malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Anhui Normal University; Hu, Yimin; Mao, Chunyan; (10 pag.)CN105523981; (2016); A;,
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Electric Literature of 117324-05-7,Some common heterocyclic compound, 117324-05-7, name is Ethyl 2-amino-4-fluorobenzoate, molecular formula is C9H10FNO2, 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.

A total of 3.84 g of 2-amino-4-fluoro-benzoic acid ethyl ester obtained in Production Example II-7-a was dissolved in 50 ml of pyridine, 1.64 ml of acetyl chloride was added under ice-cooling, and the mixture was stirred for 1 hours. The reaction mixture was diluted with water and was extracted with diethyl ether. The resulting organic layer was washed with 1 N hydrochloric acid and brine, dried over magnesium sulfate, and then evaporated, to give 4.0 g of the title compound.1H-NMR ( 400 MHz, CDCl3 ) d 1.41 ( 3H, t, J = 6.8 Hz ), 2.14 ( 3H, s ), 4.38 ( 2H, q, J = 6.8 Hz ), 6.73 – 6.81 ( 1H, m ), 8.06 ( 1H, dd, J = 8.8, 6.4 Hz ), 8.53 ( 1H, dd, J = 12.0, 2.4 Hz ), 11.3 ( 1H, brs )

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 2-amino-4-fluorobenzoate, its application will become more common.

Reference:
Patent; Eisai Co., Ltd.; EP1380576; (2004); A1;,
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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. 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H9BrO2

General procedure: A solution of TMSCl (3 mol%) in anhyd 1,4-dioxane (1 mL) wasadded to a suspension of Zn dust (2 equiv) in anhyd 1,4-dioxane(3 mL), and the resulting suspension was refluxed with vigorousstirring for 25 min. The appropriate nitrile (2 mmol) in dry 1,4-dioxane (1 mL) and ethyl (E)-4-bromobut-2-enoate (12; 2equiv) in dry 1,4-dioxane (1 mL) were simultaneously addeddropwise to the refluxing suspension during 10 min by usingtwo syringes. The resulting light-green mixture was refluxeduntil all the starting material was consumed and the colorchanged to brown (TLC; 3-6 h). The mixture was cooled to r.t.then centrifuged (700 rpm). The upper solution was decantedand the remaining solid was washed with 1,4-dioxane (4 ¡Á 1mL). The 1,4-dioxane solutions were combined and concentratedto about 1 mL under reduced pressure in a rotatory evaporator.The residue was treated with 50% aq K2CO3 until the pHreached 13 (~5 mL). The resulting mixture was stirred for 30min at r.t. (30 C) then diluted with CH2Cl2 (10 mL) and H2O (10mL). The organic layer was separated, washed sequentially withH2O (2 ¡Á 10 mL) and brine (10 mL), dried (Na2SO4), and evaporatedunder reduced pressure to give a crude product that waspurified by column chromatography [silica gel (100-200 mesh);15-60% EtOAc-hexane].

According to the analysis of related databases, 37746-78-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rao, H. Surya Prakash; Muthanna, Nandurka; Padder, Ashiq Hussain; Synlett; vol. 29; 12; (2018); p. 1649 – 1653;,
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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. 2318-25-4, name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride, A new synthetic method of this compound is introduced below., SDS of cas: 2318-25-4

Step 1: Ethyl 2-benzimidazol-2-ylacetate A solution of 1,2-phenylenediamine (1.0 equivalent) and ethyl 3-ethoxy-3-iminopropanoate hydrochloride (1.3 equivalents) in ethanol was stirred at 90¡ã C. overnight. The reaction was cooled to room temperature and the solvent was removed in vacuo. Water and CH2Cl2 were added to the residue. The organic layer was separated, dried over Na2SO4 and the solvent removed. The solid recovered was used without purification. LC/MS m/z 205.2 (MH+), Rt 1.44 minutes.

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; CHIRON CORPORATION; US2005/256157; (2005); A1;; ; Patent; Chiron Corporation; US2005/261307; (2005); 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. 64123-77-9, name is Methyl 2-(3-fluorophenyl)acetate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 2-(3-fluorophenyl)acetate

Intermediate 99: Methyl 2-chlorosulfonyl-5-fluorophenylacetate Methyl 3-fluorophenylacetate (1.51g) was added dropwise to chlorosulphonic acid (7mL) with stirring and ice cooling. The cooling bath was removed and the mixture was allowed to warm to room temperature and left to stand for 16 hours. The mixture was added toa mixture of ice and ethyl acetate and the organic layer was separated, washed with water, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane, with a gradient of 0-20%, to give methyl 2-chlorosulfonyl-5-fluorophenylacetate (1.42g) as a white solid.j00636j ?HNMR(CDC13) : 8.16 (1H, dd), 7.29-7.16 (2H, m), 4.19 (2H, s), 3.76 (3H, s).

The synthetic route of 64123-77-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZAFGEN, INC.; PALLIN, Thomas, David; CRAMP, Susan, Mary; DYKE, Hazel, Joan; ZAHLER, Robert; WO2014/71369; (2014); A1;,
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Synthetic Route of 3618-04-0, These common heterocyclic compound, 3618-04-0, name is trans-Ethyl 4-hydroxycyclohexanecarboxylate, 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.

PREPARATION 1: 1 – Allyl-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexanecarbaldehyde; Step a: 4-(/ert-Butyl-dimethyl-silanyloxy)-cyclohexanecarboxylic acid ethyl ester:; [00160] To a 50 mL flask was added 4-hydroxy-cyclohexanecarboxylic acid ethyl ester (5.0 g; 29.0 mmol), imidazole (2.37 g; 34.8 mmol), DMF (30 mL) and ter/-buryldimethylsilyl chloride (4.81 g; 32.0 mmol). The solution was stirred for 78h at 20 0C. The reaction was diluted with EtOAc (100 mL), washed with water 2 x 100 mL), brine (100 mL), dried (MgSO4) filtered and concentrated in vacuo. The crude oil was purified by flash chromatography (silica gel, hexanes/EtOAc 1:0 to 1:1) to give pure product (7.79 g, 94% yield) as a 2:1 mixture of diastereomers.1H-NMR (400 MHz, CDCl3) (J = Hz) delta mixture 4.12 (m; 2H), 3.90 (m; 0.65H), 3.58 (m; 0.35H), 2.23 (m; IH), 1.98 (m; 3H), 1.82 (m; 3H), 1.49 (m; 2H), 1.21 (m; 3H), 0.88 (s; 9H), 0.05 (s; 3H), 0.03 (s; 3H). 13C-NMR (400 MHz, CDCl3) delta mixture 175.7, 175.6, 70.5, 66.6, 60.1, 60.0, 42.2, 42.1, 34.8, 32.8, 27.2, 25.8, 25.6, 23.4, 18.2, 18.0, 14.2, -4.7, -4.9. MS (ES+) m/z 287.22 [MH+].

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

Reference:
Patent; BIOGEN IDEC MA INC; WO2007/76086; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 36692-49-6, 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 36692-49-6 as follows.

Example 96; (2Z,5Z)-2-[(2,6-dichlorophenyl)imino]-5-{[2-(1-methylethyl)-1H-benzimidazol-6-yl ]methylidene}-1,3-thiazolidin-4-one; (a) methyl 2- (1-methylethyl)-lHbenzimidazole-6-carboxylate; A solution of isobutyraldehyde (0.22 mL, 2.41 mmol) and 40 % aq. sodium hydrogen sulfite (2.6 mL) was stirred at room temperature for 1 h. To this mixture is added a solution of methyl 3,4-diaminobenzoate (0.400 g, 2.41 mmol) in ethanol (2 mL). The resulting solution is heated to reflux overnight. The mixture was diluted in water and the resulting precipitate was collected by filtration to obtain 0.524 g of the desired product in >99 % yield. The crude was used without further purification. [MS (ES+) m/e 219 M+H] +. 1H NMR (400 MHz, CHLOROFORM-d) 8 ppm 8.30 (d, =7=1. 0 Hz, 1 H) 7.93 (dd, J=8. 6,1. 5 Hz, 1 H) 7.54 (d, 8. 6 Hz, 1 H) 3.90 (s, 3 H) 3.30-3. 41 (m, 1 H) 1. 48 (d, 7. 1 Hz, 6 H).

According to the analysis of related databases, 36692-49-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/82901; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics