Synthetic Route of 558-42-9, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 558-42-9, name is 1-Chloro-2-methyl-2-propanol, molecular formula is C4H9ClO, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
[00296j Step 1: methyl 6-chloro-5-(2-hydroxy-2-methyl-propoxy)pyridine-2-carboxylate [00297j A solution of methyl 6-chloro-5 -hydroxy-pyridine-2- carboxylate (1.6 g, 8.3 mmol) in methanol (1.5 mL) was treated with finely ground potassium carbonate (4.6 g, 33.0 mmol). The reaction mixture was heated to 80 °C and1-chloro-2-methyl-propan-2-ol (1.7 mL, 16.5 mmol) was added. The reaction mixture was heated at 80 °C overnight. The reaction mixture was concentrated under reduced pressure. The remaining residue was suspended in water (75 mL) and extracted with ethyl acetate (2 x 75 mL). Organic layers were combined, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting oil was purified bysilica gel colunm chromatography: 40 gram silica gel column, 0-30percent ethyl acetate/hexane gradient over 25 mm to afford methyl 6-chloro-5-(2-hydroxy-2-methyl- propoxy)pyridine-2-carboxylate (1.2 g, 54percent) was obtained as a colorless solid. ?H NMR (400 MHz, CDC13) oe 8.09 (d, J = 8.4 Hz, 1H), 7.27 (d, J = 8.4 Hz, 1H), 3.98 (s, 3H), 3.94 (s, 2H), 1.41 (s, 6H). ESI-MS mlz calc. 259.1, found 260.2 (M+1)+;Retention time: 0.99 mm (3 mm run).
According to the analysis of related databases, 558-42-9, the application of this compound in the production field has become more and more popular.
Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; DENINNO, Michael, Paul; ANDERSON, Corey; CONROY, Erica, Lynn; FRIEMAN, Bryan, A.; GROOTHENHUIS, Peter, Diederik Jan; HADIDA-RUAH, Sara, Sabina; HURLEY, Dennis, James; PIERRE, Fabrice Jean, Denis; SILINA, Alina; UY, Johnny; ZHOU, Jinglan; WO2015/6280; (2015); A1;,
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