Sodium Hydroxide → (2-Methylpropoxy)methyl boronic acid

To a solution of tributyl-(2-methylpropoxy)methyl-tin (1.00 g, 2.65 mmol) in tetrahydrofuran (20 ml) was added dropwise n-butyllithium (1.54M n-hexane solution, 1.72 ml, 2.65 mmol) at −78° C. (external temperature) under the nitrogen atmosphere, and the reaction mixture was stirred at the same temperature for 35 minutes. Then, to the reaction mixture was added triisopropyl borate (1.10 ml, 4.74 mmol) at −78° C. (external temperature) under the nitrogen atmosphere, and the reaction mixture was stirred at room temperature for 50 minutes. To the reaction mixture was added a 1N aqueous sodium hydroxide solution at room temperature. The resultant was extracted three times, and the resulting aqueous layer was washed with diethyl ether. Then, to the resulting aqueous layer was added 5N aqueous hydrochloric acid solution to make the solution acidic, followed by extraction with diethyl ether three times. The resulting organic layer was washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and filtered. The solvent was distilled off from the filtrate to obtain the title compound (101 mg, 0.765 mmol, 29%).

1. stirringthe reaction mixture was stirred at room temperature for 50 minutes
2. extractionThe resultant was extracted three times
3. washthe resulting aqueous layer was washed with diethyl ether
4. additionThen, to the resulting aqueous layer was added 5N aqueous hydrochloric acid solution
5. extractionfollowed by extraction with diethyl ether three times
6. washThe resulting organic layer was washed with an aqueous saturated sodium chloride solution
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationfiltered
9. distillationThe solvent was distilled off from the filtrate

ORD record

ord-79933816bcf14e2d9386197eda196950

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696347B2