Acetic Acid → 6-Methoxy-2,3-dihydro-benzo[1,4]dioxin-5-yl-boronic acid

To a solution of methyl ether X (10.0 g, 60 mmol) in 50 ml THF at −78° C. was added n-butyllithium (36 ml, 90 mmol, 2.5 M in hexanes) was added drop-wise. After 1 h the solution was warmed to rt. After 1 h the solution was cooled to −78° C. and trimethyl borate (13.6 ml, 120 mmol) was added. The solution was warmed to rt. After 16 h the mixture was quenched by the addition of water and resulting mixture was acidified with AcOH and extracted with ethyl acetate. The combined organics were washed with saturated NaHCO3, dried with MgSO4, filtered and concentrated in vacuo. The resulting oil was azeotroped with toluene to afford 6-methoxy-2,3-dihydro-benzo[1,4]dioxin-5-yl-boronic acid (13.72 g, 98%) as an oil.

1. additionwas added drop-wise
2. temperatureAfter 1 h the solution was cooled to −78° C.
3. temperatureThe solution was warmed to rt
4. customAfter 16 h the mixture was quenched by the addition of water
5. customresulting mixture
6. extractionextracted with ethyl acetate
7. washThe combined organics were washed with saturated NaHCO3
8. dry with materialdried with MgSO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe resulting oil was azeotroped with toluene

ORD-Eintrag

ord-fa46b96d7c94484c9ac890e640e88cc9

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08846705B2