Diethyl Ether → 2-[5-(Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]propan-2-ol

To a solution of methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinate (Frontier, catalog No. M2012) (1.25 g, 4.75 mmol) in THF (48 mL) was added a solution of methyl magnesium bromide in ethyl ether (3.0 M, 12 mL, 36 mmol) via syringe at 0° C. with an ice water bath under dry N2. The reaction mixture was added at 0° C. for 30 minutes and then the ice-water bath was removed. After stirring at room temperature for 30 minutes, the reaction mixture was poured into saturated NH4Cl solution (300 mL) and followed by addition of 100 mL of EtOAc. The organic phase was separated and the aqueous phase was extracted with EtOAc (2×50 mL). The combined organic phases were washed with brine (10 mL), dried over Na2SO4, and evaporated to afford crude title compound that was used directly in the next step reaction.

1. additionThe reaction mixture was added at 0° C. for 30 minutes
2. customthe ice-water bath was removed
3. additionthe reaction mixture was poured into saturated NH4Cl solution (300 mL)
4. additionfollowed by addition of 100 mL of EtOAc
5. customThe organic phase was separated
6. extractionthe aqueous phase was extracted with EtOAc (2×50 mL)
7. washThe combined organic phases were washed with brine (10 mL)
8. dry with materialdried over Na2SO4
9. customevaporated

ORD record

ord-0dd31a0b154f4e32b008e89dbcdc6af8

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354526B2