Extracurricular laboratory: Synthetic route of Isopropyl glycolate

The synthetic route of 623-61-0 has been constantly updated, and we look forward to future research findings.

Adding a certain compound to certain chemical reactions, such as: 623-61-0, Isopropyl glycolate, 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, name: Isopropyl glycolate, blongs to alcohols-buliding-blocks compound. name: Isopropyl glycolate

General procedure: The nucleoside (3.21 mmol) was suspended in THF (25 ml). Under nitrogen and at 0 C., POCl3 (4.82 mmol) was added and the reaction mixture was allowed to reach at room temperature overnight. The reaction mixture was cooled down to 0 C. and a mixture of alcohol (3.53 mmol) and TEA (16.06 mmol) in CH3CN (10 ml) was added dropwise. The mixture was stirred at 0 C. during 1 hour. N-Methylimidazole (19.27 mmol) was added at 0 C. and after 15 min at 0 C., the reaction mixture was stirred at room temperature during 2 hours. The mixture was quenched on a solution 0.5M phosphate buffer (pH=7) and the product was extracted with CH2Cl2. The organic layer was dried on Na2SO4, filtered and concentrated under reduced pressure. The crude was purified by silica gel chromatography (eluent: CH2Cl2/CH3CH2OH 0 to 20%) and by preparative MS/HPLC to give the expected compounds as a mixture of diastereoisomers. White solid; 1H NMR (DMSO-d6, 400 MHz) delta (ppm) 0.95 (s, 3H), 1.21-1.23 (m, 6H), 3.95 (s, 3H), 4.22-4.29 (m, 0.7H), 4.46-4.53 (m, 0.3H), 4.63-4.75 (m, 4H), 4.96-5.03 (m, 1H), 5.93 (brs, 1H), 6.07 (brs, 0.3H), 6.14 (brs, 0.7H), 6.48 (brs, 1H), 6.59 (s, 1H), 8.05 (s, 0.7H), 8.12 (brs, 0.3H); 31P NMR (DMSO-d6, 162 MHz) delta (ppm)-5.84 (s, 0.68P), -5.01 (s, 0.32P); MS (ESI) m/z=474.2 (MH+).

The synthetic route of 623-61-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PARSY, Christophe Claude; ALEXANDRE, Francois-Rene; DOUSSON, Cyril B.; DUKHAN, David; GOSSELIN, Gilles; RAHALI, Houcine; SURLERAUX, Dominique; US2013/315867; (2013); A1;,
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