Synthesis method of hydroxypropyl tetrahydropyrantriol
A technology for synthesizing hydroxypropyltetrahydropyranotriol and hydroxypropyl, which is applied in the direction of organic chemistry methods, chemical instruments and methods, and compounds containing Group 3/13 elements of the periodic table, etc., which can solve the problems of purification and production Low yield/yield, complicated operation, etc., to achieve the effect of high product yield, good quality, and simple reaction process
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Embodiment 1
[0045] Preparation of compound II: Example 1
[0046]13.9 g of 1-bromo-2-hydroxypropane, 8.2 g of imidazole and 200 ml of dichloromethane solvent was added to the glass reactor, and electron stirred under nitrogen protection, then 18.1 gtbscl (tert-butyl dimethyl) was added in batches. Chlorosilane). After the addition, the temperature was stirred overnight, and the TLC was tested and the reaction was washed with saturated brine, and 21.1 g of a colorless oil (1-bromo-isopropyl) tert-butyl dimethylideilaptic ether can be obtained after concentration.
[0047] 10.1 g (1-bromo-isopropyl) tert-butyl dimethylsilaty ether was added to the glass reactor, 50 ml of anhydrous tetrahydrofuran, nitrogen protection decreased temperature dropped to -40 ° C, 0.2 ml of 2m isopropyl chloride Tetrahydrofuran solution to the system. The mixture was stirred at -40 ° C for 2 hours, and 5 g of trimethyl borate was added to the system, and the stirring reaction was completed. After quenching the reacti...
Embodiment 2
[0049] Example 2: Preparation of hydroxypropyl tetrahydropyran triol
[0050] 10.0 g (46.9 mmol) of Compound I, 5.3 g (51.6 mmol) II ((2-hydroxypropyl) boric acid), 10.0 g of water and 20.0 g tetrahydrofuran were added to a glass reactor. The reaction system was inerted with argon and protected by micro-gas flow. Palladium chloride was added 0.08 g (0.47 mmol) and potassium carbonate under argon, and 12.9 g (93.8 mmol), 0.2 g (0.47 mmol) MOR-DALPHOS was added as a ligand, and 55-60 ° C reaction was completed after 6 hours. The use of activated carbon to dissolve the hydroxypropyl tetrahydropyraniol 7.4 g of colorless syrup graphiciol, and the yield is 82%.
[0051] according to figure 1 Nuclear magnetic carbon spectrum and figure 2 The HPLC spectrum can determine that the product is a target product hydroxypropyl tetrahydropyraniol, that is, a glass.
Embodiment 3
[0052] Example 3: Preparation of hydroxypropyl tetrahydropyran triol
[0053] 15.0 g (70.4 mmol) of Compound I, 8.0 g (77.4 mmol) II ((2-hydroxypropyl) boric acid), 15.0 g of water and 30.0 g of isopropanol were added to the glass reactor. The reaction system was inerted with argon and protected by micro-gas flow. Palladium chloride was added to 0.12 g (0.7 mmol) and sodium carbonate under argon, and 0.29 g (0.7 mmol) Me-Dalphos was added as a ligand, 60-65 ° C for 8 hours after 8 hours. The hydroxypropyl tetrahydropyraniol 11.5 g of colorless syrup products can be obtained from the system with activated carbon. The yield is 85%.
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