Category: 115754-62-6

115754-62-6, ((1,3-Dioxolan-2-yl)methyl)tributylphosphonium bromide is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a mixture of 8a (0.18g, 1.44mmol) and 1,3-dioxolan-2-ylmethyltributylphosphonium bromide (10) (0.28g, 0.75mmol) in dry DMF (3mL) a 0.48M solution of sodium ethoxide in ethanol (1.5mL, 0.73mmol) was added under argon atmosphere. The mixture was stirred at 90C for 22h and then water (75mL) was added. The aqueous phase was extracted with AcOEt (4¡Á50mL), and the resulting organic layer was washed with brine, dried over MgSO4, and evaporated. To a solution of the crude residue in THF (10mL), an aqueous solution of HCl 1N (40mL) was added and the mixture was stirred for 90min at room temperature. Then, water (50mL) was added and the aqueous phase was extracted with AcOEt (4¡Á50mL). The organic layer was dried over MgSO4 and evaporated. The crude product was purified by flash column chromatography (silicagel) using CH2Cl2/ hexane (9:1) as eluent, yielding 8b (0.14g, 0.34mmol, 72%) as a dark red solid. Found: C 73.55, H 3.90. C27H18O2S2 requires C 73.94, H 4.14%. Mp 220-222C. IR (KBr, cm-1): 1651 (C=O), 1600 (C=C), 1552 (C=C). 1H NMR (300MHz, CDCl3): delta 9.63 (d, J=7.7Hz, 1H, -CHO), 7.89-7.83 (m, 2H, phenyl-H), 7.81-7.75 (m, 2H, phenyl-H), 7.61 (d, J=15.3Hz, 1H, -CH=CH-CHO), 7.54-7.40 (m, 7H, phenyl-H+TT-H), 7.16 (d, J=2.1Hz, 1H, pyranylidene-H), 7.08 (br s, 1H, pyranylidene-H), 6.48 (s, 1H, TT-H), 6.47 (dd, J1=15.3 Hz, J2=7.7Hz, 1H, -CH=CH-CHO), 6.14 (s, 1H, pyranylidene=C-H). 13C NMR (100MHz, CDCl3): delta 192.5, 185.9, 154.2, 151.9, 148.7, 145.0, 139.5, 133.0, 132.8, 130.5, 129.9, 129.4, 128.8, 128.7, 125.7, 125.1, 125.0, 124.8, 124.6, 116.5, 108.5, 107.6, 102.7. HRMS (ESI+): found 439.0804 [M+H]+. C27H19O2S2 requires 439.0821., 115754-62-6

As the paragraph descriping shows that 115754-62-6 is playing an increasingly important role.

Reference£º
Article; Marco, A. Belen; Andreu, Raquel; Franco, Santiago; Garin, Javier; Orduna, Jesus; Villacampa, Belen; Alicante, Raquel; Tetrahedron; vol. 69; 19; (2013); p. 3919 – 3926;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

115754-62-6, ((1,3-Dioxolan-2-yl)methyl)tributylphosphonium bromide is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

3,5-dibromobenzaldehyde (16.1 g, 61.0 mmol) was added to a cold (ice-water bath) solution of tert-butoxide (13.0 g, 116 mmol), (l,3-dioxolan-2-ylmethyl)tri-n-butylphosphine bromide salt (4.5 M, 32 cm3, 144 mmol) in 400 cm3 of ether under argon. The mixture was stirred at 0-2 C for 2 h. 1.0 M HCl(aq) (300 cm3) was added to the mixture. The reaction was gradually warmed to room temperature and stirred at room temperature for 21 h. The two layers were separated. The aqueous layer was extracted with ether (3 x 200 cm3). The organic layer and the ether extracts were combined, washed with brine (1 x 300 cm3) and dried over anhydrous magnesium sulfate. The solvents were completely removed to leave a yellow solid. The solid was purified by column chromatography of silica gel using ethyl acetate-light petroleum (40-60 C) as eluent to give 3.36 g (19%) of A-1 as a colourless solid; deltaH(200 MHz; CDCl3) 6.68 (1 H, dd, J1A & 16 Hz, vinylH), 7.33 (1 H, d, J16 Hz, vinylH), 7.33 (2 H, m, ArH), 7.63 (1 H, m, ArH), and 9.72 (1 H, d, J7.6 Hz, CHO); m/z [CI(NH3)] 306, 308, 310 (MNH4+), and 288, 290, 292 (M+)., 115754-62-6

The synthetic route of 115754-62-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; ISIS INNOVATION LIMITED; THE UNIVERSITY COURT OF THE UNIVERSTIY OF ST ANDREWS; WO2004/20448; (2004); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

115754-62-6, ((1,3-Dioxolan-2-yl)methyl)tributylphosphonium bromide is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,115754-62-6

General procedure: The compounds 4ab were synthesized via modified literature procedure [34]. Aldehyde 3a or 3b (2 mmol) and tributyl(1,3- dioxolan-2-ylmethyl)phosphonium bromide (1.63 g, 4.4 mmol) were dissolved in dry THF (50 mL). Argon was bubbled through the solution for 15 min, NaH (144 mg, 6 mmol) was added and the reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (3 100 mL). The combined organic layers were dried (Na2SO4) and the solvents were evaporated in vacuo. The residue was dissolved in THF (100 mL), 12% HCl (50 mL) was added and the solution was stirred for 1 h. The reaction mixture was diluted with water (100 mL) and extracted with EtOAc (3 100 mL). Both products 4a and 4b are sparingly soluble in common organic solvents. Therefore, the collected organic suspensions was concentrated in vacuo and precipitate was filtered off. The crude product 4a or 4b was suspended in EtOAc (50 mL), the suspension was refluxed for 30 min, cooled to 25 C and the product was isolated by filtration. After drying, products 4a and 4b were used in the following reaction step without further purification. A full purification of small quantities is possible by column chromatography (SiO2, CH2Cl2/EtOAc 10:1) using large excess of the eluting solvents.

115754-62-6 ((1,3-Dioxolan-2-yl)methyl)tributylphosphonium bromide 22292430, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Article; Speratova, Michaela; Jedyrka, Jaroslaw; Pytela, Old?ich; Kityk, Iwan V.; Reshak; Bure?; Klikar; Tetrahedron; vol. 75; 34; (2019);,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.115754-62-6,((1,3-Dioxolan-2-yl)methyl)tributylphosphonium bromide,as a common compound, the synthetic route is as follows.

5.0 g (0.02548 mol) of 3,4,5-trimethoxy benzaldehyde and 33 ml of a 1M solution of previously made Wittig Salt III [4] in dimethylformamide (DMF) (1.3 equivalents, 0.03312 mol) was added to 150 ml 95% EtOH under N2 and warmed to dissolve all solids. 19 ml 2M NaOEt (1.5 equivalents, 0.03822 mol) was added drop-wise, and the reaction was heated to 60 C. for 48 hours. The mixture was poured into 300 ml H2O, extracted with 3¡Á75 ml EtOAc, washed with 2¡Á40 ml H2O and 2¡Á40 ml brine, dried with MgSO4, and concentrated by rotary evaporation. The resulting yellow solids were added to 150 ml THF. 100 ml 2M HCl was added to this solution and stirred for one hour at 20 C. Most of the solvent was removed by rotary evaporation, and the remainder was poured into 100 ml H2O. The product was extracted, washed, and dried as before, giving 5.2 g of impure yellow oil. This oil was purified through a short silica gel column, eluting with CH2Cl2 giving 4.02 g of a yellow solid, (E)-4-(3,4,5-trimethoxyphenyl)but-3-en-2-one intermediate product. The total yield was 4.02 g or 71%.1H NMR (500 MHz, CDCl3), delta 9.66 (d, J=8 Hz, 1H), 7.37 (d, J=16 Hz, 1H), 6.77 (s, 2H), 6.62 (dd, J=16 Hz, J=8 Hz, 1H), 3.88 (s, 9H), 115754-62-6

115754-62-6 ((1,3-Dioxolan-2-yl)methyl)tributylphosphonium bromide 22292430, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Patent; Spangler, Brenda D.; Spangler, Charles W.; Tarter, E. Scott; US2009/43109; (2009); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI