Reacción #42733

Ecuación de reacción

product

6-Bromoacetyl-2,2-dimethyl-4H-benzo[1,3]dioxine

BH3-THF

→

title compound

(R)-2-Bromo-1-(2,2-dimethyl-4H-benzo[1,3]dioxin-6-yl)ethanol

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solid catalyst of Preparation 13, step (c)(1) (0.97 g, 3.5 mmol)
2. 2
   TemperaturaThe solution was cooled to between −20° C. and −10° C.
3. 3
   workup.ADDITIONwas added dropwise via a dropping funnel
4. 4
   workup.ADDITIONAfter the addition
5. 5
   Otrothe reaction mixture was quenched by slow addition of 50 mL of methanol
6. 6
   Concentraciónconcentrated to a thick oil
7. 7
   OtroThe oil was purified by silica gel chromatography
8. 8
   Lavadoeluted with 1:2 ethyl acetate/hexanes
9. 9
   Concentraciónconcentrated

Procedimiento

To the product of step (c) (10 g, 35.1 mmol) in 100 mL of THF was added the solid catalyst of Preparation 13, step (c)(1) (0.97 g, 3.5 mmol). The solution was cooled to between −20° C. and −10° C. and BH3-THF (35 mL, 35 mmol) diluted with 50 mL THF was added dropwise via a dropping funnel. After the addition was complete, the reaction mixture was allowed to warm to ambient temperature. After 30 minutes, the reaction mixture was quenched by slow addition of 50 mL of methanol and then concentrated to a thick oil. The oil was purified by silica gel chromatography eluted with 1:2 ethyl acetate/hexanes. The fractions were combined and concentrated to give the title compound as an off-white solid.

Fuente