Reacción #48333

Ecuación de reacción

HCl

borane-dimethyl sulfide

THF

6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-one

(s)-2-methyl-cbs-oxazaborolidine

→

title compound

(4R)-6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-ol

Disolventes

toluene

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto quench
2. 2
   Otrothe reaction
3. 3
   ExtracciónThe resulted mixture was extracted with EtOAc
4. 4
   LavadoThe organic layer was washed with water and brine
5. 5
   Secadodried over Na2SO4
6. 6
   Filtraciónfiltered
7. 7
   Concentraciónconcentrated
8. 8
   OtroThe residue was purified on silica gel column

Procedimiento

To a cooled (ice bath) solution of (s)-2-methyl-cbs-oxazaborolidine 1.0 M in toluene (100 μl, 100 μmol) was added borane-dimethyl sulfide 2.0 M in THF (500 μl, 1000 μmol). After stirred 15 min, a solution of 6-bromo-2-methyl-2-(trifluoromethyl)chroman-4-one (309 mg, 1000 μmol) in toluene was added drop wise. The reaction was completed after stirring 9h at 0° C. 2N HCl was added slowly to quench the reaction. The resulted mixture was extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified on silica gel column to afford the title compound.

Fuente