Reacción #1973988

Ecuación de reacción

5-bromo-2,3-dihydro-1H-inden-1-one

sodium borohydride

→

title compound

Rendimiento 145.9%

5-bromo-2,3-dihydro-1H-inden-1-ol

Rendimiento 145.9%

Disolventes

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITAfter a few minutes
2. 2
   Temperaturathe solution warmed slightly
3. 3
   workup.DISSOLUTIONall solids dissolved
4. 4
   Concentraciónthe mixture was concentrated in vacuo
5. 5
   Otroto remove ethanol
6. 6
   OtroThe gum obtained
7. 7
   Otrowas partitioned between ethyl acetate and water
8. 8
   ExtracciónThe organic layer was extracted with saturated sodium bicarbonate solution (2×) and saturated sodium chloride solution
9. 9
   OtroDrying
10. 10
    Concentración(Na2SO4) and concentration in vacuo

Procedimiento

A suspension of 5-bromo-2,3-dihydro-1H-inden-1-one (2.07 g, 9.81 mmol) in ethanol (49 mL) was treated with the sodium borohydride (186 mg, 4.90 mmol) all at once. After a few minutes, the solution warmed slightly and all solids dissolved. After stirring at room temperature for 1 h, the mixture was concentrated in vacuo to remove ethanol. The gum obtained was partitioned between ethyl acetate and water. The organic layer was extracted with saturated sodium bicarbonate solution (2×) and saturated sodium chloride solution. Drying (Na2SO4) and concentration in vacuo afforded the title compound (3.05 g, 98%) as a colorless oil, which crystallized upon pumping under high vacuum overnight.

Fuente