Triisopropyl borate → 2,6-Dimethoxy-4-methoxymethylphenylboric acid

To a solution of 3,5-dimethoxy(methoxymethyl)benzene (23.7 g) in tetrahydrofuran (500 mL) was added n-butyllithium (1.56M hexane solution; 100 mL) at −78° C., and the reaction mixture was stirred for 30 minutes while cooling with ice. After cooling the internal temperature of the obtained reaction mixture to −78° C., to a reaction mixture was added triisopropoxyborane (39 mL), and the internal 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 then ethyl acetate was added to the reaction mixture, the organic extract was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography and the title compound (7.5 g) was obtained as a yellow oil from the ethyl acetate fraction.

1. temperaturewhile cooling with ice
2. temperatureAfter cooling
3. customthe internal temperature of the obtained reaction mixture to −78° C.
4. stirringwhile stirring
5. additionwas added to the reaction mixture
6. temperaturewhile cooling with ice
7. extractionthe organic extract
8. washwas washed with brine
9. dry with materialdried over anhydrous magnesium sulfate
10. customthe solvent was evaporated under reduced pressure
11. customThe residue was purified by silica gel column chromatography

ORD record

ord-a0ecb90d07af4a3f8329a3cbccacfce1

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07176216B2