Triethyl borate → HCID 23080943, compound

To a solution of 3,5-dimethoxybenzyl alcohol (2.71 g) in tetrahydrofuran (50 mL) was added n-butyllithium (1.56M hexane solution; 36.2 mL)while cooling with ice with ice bath, and the internal temperature was raised to room temperature and stirred for 1 hour. The internal temperature was then cooled to −78° C., to the mixture was added triethoxyborane (9.6 mL), and the temperature was raised to room temperature while stirring. After completion of the reaction, saturated aqueous ammonium chloride was added to the reaction mixture while cooling with ice and the reaction mixture was extracted with ethyl acetate, and then after washing the organic extract with brine, it was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (50 g) and the title compound (1.72 g) was obtained as a white amorphous solid from the ethyl acetate fraction.

1. temperaturewhile cooling with ice with ice bath
2. temperatureThe internal temperature was then cooled to −78° C., to the mixture
3. temperaturethe temperature was raised to room temperature
4. stirringwhile stirring
5. additionwas added to the reaction mixture
6. temperaturewhile cooling with ice
7. extractionthe reaction mixture was extracted with ethyl acetate
8. washafter washing the
9. extractionorganic extract with brine, it
10. dry with materialwas dried over anhydrous magnesium sulfate
11. customthe solvent was evaporated under reduced pressure
12. customThe residue was purified by silica gel column chromatography (50 g)

ORD record

ord-f697dda9c2e447db89275263f5a948cc

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07176216B2