Adding a certain compound to certain chemical reactions, such as: 31930-34-4, name is Ethyl cis-3-Bromoacrylate, 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 31930-34-4, 31930-34-4
General procedure: Pd(PPh3)4 (0.047g, 0.042 mmol) and CuI (0.016g, mmol) were dissolved in degassed NEt3 (11 mL). (Z)- Ethyl 3-bromopropenoate1 (0.75 g, 4.2mmol) was dissolved in degassed NEt3 (1.8 mL) and slowly added to the reaction mixture. After 5 minutes, propargyl alcohol (0.23 g, 4.1 mmol) in degassed NEt3 (1.8 mL) was added dropwise and the mixture was stirred for 24 h. The contents of the flask were filtered through Celite and washed with hexanes. Saturated NH4Cl solution was added to the filtrate, which was subjected to a conventional extractive workup (CH2Cl2)(3x). The residue (0.250 g, 1.62 mmol) was dissolved in 50 mL of CH2Cl2 (50 mL) and the solution was cooled to 0 C. Excess Co2(CO)8 was added to the flask and the mixture was stirred for 30 minutes. The solution was removed from the ice bath and allowed to come to room temperature while stirring for an additional 2 h. Following solvent removal under reduced pressure, the crude product was dissolved in petroleum ether and filtered through a silica plug. The silica gel was first washed with petroleum ether to flush out excess Co2(CO)8 and then washed with diethyl ether to collect hexacarbonyl [mu-eta4((Z)- ethyl 6-hydroxyhex-2-en-4-ynoate)]dicobalt (1.103 g, 60%). IR (neat): 3465, 2984, 2902, 2051, 2002, 1704; 1H NMR : 7.03 (d, J=11.4, 1H), 5.88 (d,J=11.4, 1H), 4.87 (d, J=6.9, 2H), 4.17 (q, J=7.2, 2H), 4.11 (t, J=6.9, 1H), 1.26 (t, J=7.2, 3H); 13C NMR :198.8, 166.4, 142.8, 117.2, 98.0, 79.8, 64.5, 60.64, 14.0; MS EI m/e: 384 (M+ -2CO), 356 (M+ – 3CO), 328(M+ – 4CO), 272 (M+ – 6CO); HRMS for C14H10Co2O9, calcd (M+-2CO) 383.9090, found 383.9091.To a solution of hexacarbonyl[mu-eta4((Z)- ethyl 6-hydroxyhex-2-en-4-ynoate)]dicobalt (0.363 g,0824 mmol) was stirred in acetic anhydride (1.5 mL) and pyridine (1.5 mL), starting at 0C and warming up to room temperature. After 2 hours, the reaction was placed under reduced pressure to obtain crude product and flash chromatography was performed (10:1 petroleum ether: diethyl ether) to yield (10) as a dark red oil (0.3599 g, 91%). IR (neat) 2960, 2094, 2054, 2019, 1744, 1719; 1H NMR : 7.07 (d, J = 11.4,1H), 5.93 (d, J = 11.4, 1H), 5.478 (s, 2H), 4.18 (q, J = 7.1, 2H), 2.14 (s, 3H), 1.29 (t, J = 7.1, 3H); 13C NMR :198.8, 170.8, 165.1, 141.6, 118.5, 109.6, 93.8, 79.7, 66.2, 60.3, 20.5, 14.2; MS EI m/e: 398 (M+ – 3CO),370 (M+ – 4CO), 342 (M+ – 5CO), 314 (M+ – 6CO); HRMS for C16H12Co2O10, calcd (M+-3CO) 397.9247,found 397.9262.
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, Ethyl cis-3-Bromoacrylate, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Mahmood, Aqsa; Ngenzi, Rebecca; Penner, Page M.; Green, James R.; Synlett; vol. 27; 8; (2016); p. 1245 – 1250;,
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