Category: 85920-63-4

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. 85920-63-4, name is 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione, A new synthetic method of this compound is introduced below., COA of Formula: C8H10O5

General procedure: To a round bottomed flask equipped with a magnetic bar, benzaldehyde 2a (200 mg, 1.15 mmol) and freshly prepared benzoyl Meldrum?s acid 4a (430 mg, 1.73 mmol) were added in 2 mL THF-H2O (5:1). Then the catalyst DMEDA (25 mL, 0.23 mmol) was added and the reaction mixture was allowed to stir for 12 h at 55 C. After the complete consumption of benzaldehyde 2a (monitored by TLC), reaction mixture was filtered through anhydrous Na2SO4 and the residue was purified by column chromatography over silica gel using ethyl acetate in petroleum ether as eluent. The product 5a was obtained as pale yellow viscous oil in 82% yield (261 mg).

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:
Article; Khopade, Tushar M.; Warghude, Prakash K.; Mete, Trimbak B.; Bhat, Ramakrishna G.; Tetrahedron Letters; vol. 60; 2; (2019); p. 197 – 200;,
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

Synthetic Route of 85920-63-4, These common heterocyclic compound, 85920-63-4, name is 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione, 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.

Enaminone 15 (3.0 g, 15.7 mmol, 1.0 equiv.) and freshly ground acyl Meldrum’s acid (8.76 g, 47.1 mmol, 3.0 equiv.) were dissolved in toluene (157 mL) and the solution was heated to reflux for 45 min. Removal of the volatiles yielded a brown semisolid. The crude material was purified using acidified silica gel* and 7:1 hexanes: ethyl acetate as the eluent to afford 14 as a white solid (1.55?g, 6.73?mmol, 43%).

The synthetic route of 85920-63-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Eliasen, Anders M.; Chin, Matthew R.; Axelrod, Abram J.; Abagyan, Ruben; Siegel, Dionicio; Tetrahedron; vol. 74; 26; (2018); p. 3238 – 3245;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

85920-63-4, Name is 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione, 85920-63-4, 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.

Acetyl-Meldrum?s acid (309 mg, 1.66 mmol) was added to a solution of the denosylated precursor from the preceding reaction (300 mg, 663 mumol) in dioxane (15 mL). The reaction was stirred for 90 min at 80 C. Then a solution of KOH in MeOH (0.1 M, 16.6 mL, 1.66 mmol) was added and stirring was continued for another 60 min at 80 C. The solvent was removed under reduced pressure and the residue separated between DCM and aqueous ammonium chloride. The aqueous phase was extracted twice with DCM and the combined organic layers were dried over Na2SO4. Filtration and evaporation of the solvent under reduced pressure gave a crude product (347 mg), which yielded 16 (260, 80%) as a 1:1 mixture of diastereomers after chromatographic purification (DCM/MeOH 25/1). The diastereomers of a small sample were separated by semipreparative HPLC (ACN/H2O 70/30). Rf (DCM/MeOH 95/5): 0.45. (6aR,11aS,11bR)-N-tosyl-CPA 16a (cis-C/D ring connection): 1H NMR (600 MHz; CDCl3): delta=7.85 (d, J=8.4 Hz, 2H), 7.78 (d, J=8.3 Hz, 1H), 7.55 (s, 1H), 7.30-7.27 (m, 1H), 7.25 (d, J=8.2 Hz, 2H), 7.05 (d, J=7.3 Hz, 1H), 4.00 (d, J=10.9 Hz, 1H), 3.58 (dd, J=10.9, 6.0 Hz, 1H), 3.02 (dd, J=16.3, 5.8 Hz, 1H), 2.94 (dd, J=16.1, 11.7 Hz, 1H), 2.59 (Psidt, J=11.6, 5.9, 5.9 Hz, 1H), 2.49 (s, 3H), 2.36 (s, 3H), 1.67 (s, 3H), 1.58 (s, 3H); 13C NMR (125 MHz; CDCl3): delta=194.3, 185.0, 175.4, 144.7, 135.6, 133.1, 129.8 (CH), 129.3, 128.4, 126.9 (CH), 125.5 (CH), 122.9 (CH), 120.6 (CH), 116.2, 111.6 (CH), 105.4, 70.7 (CH), 63.6, 52.4 (CH), 35.4 (CH), 26.1 (CH3), 26.1 (CH2), 24.4 (CH3), 21.5 (CH3), 19.8 (CH3); HR-ES-MS: m/z=513.1449 (calcd 513.1455 for C27H26N2NaO5S); IR: nu=3415, 1709, 1614 cm-1. (6aS,11aS,11bR)-N-Tosyl-CPA 16b (trans-C/D ring connection): 1H NMR (600 MHz; CDCl3): delta=7.85 (d, J=8.4 Hz, 2H), 7.82 (d, J=8.2 Hz, 1H), 7.55 (d, J=1.7 Hz, 1H), 7.29 (Psit, J=7.8 Hz, 1H), 7.25 (d, J=8.1 Hz, 2H), 7.06 (d, J=7.3 Hz, 1H), 4.09 (d, J=10.7 Hz, 1H), 2.95 (Psidt, J=11.4, 1.7 Hz, 1H), 2.92 (dd, J=15.6, 4.6 Hz, 1H), 2.88 (dd, J=15.5, 11.8 Hz, 1H), 2.52 (s, 3H), 2.37 (s, 3H), 2.32, (Psidt, J=11.8, 11.8, 4.6 Hz, 1H), 1.60 (s, 3H), 1.53 (s, 3H); 13C NMR (125 MHz; CDCl3): delta=193.6, 185.6, 174.6, 144.7, 135.7, 133.7, 130.9 (CH), 129.9, 129.4, 126.9 (CH), 125.6 (CH), 121.3 (CH), 121.2 (CH), 118.0, 111.9 (CH), 105.3, 71.2 (CH), 62.1, 58.0 (CH), 38.4 (CH), 28.0 (CH3), 27.2 (CH2), 21.5 (CH3), 19.8 (CH3), 19.7 (CH3); HR-ES-MS: m/z=489.1497 (calcd 489.1490 for C27H25N2O5S); IR: nu=3362, 1611 cm-1.

Statistics shows that 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione is playing an increasingly important role. we look forward to future research findings about 85920-63-4.

Reference:
Article; Beyer, W.R. Christian; Woithe, Katharina; Lueke, Bettina; Schindler, Michael; Antonicek, Horst; Scherkenbeck, Juergen; Tetrahedron; vol. 67; 17; (2011); p. 3062 – 3070;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics