Реакция #1973988

Уравнение реакции

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

sodium borohydride

→

title compound

Выход 145.9%

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

Выход 145.9%

Растворители

ethanol

Условия реакции

Обработка

1. 1
   workup.WAITAfter a few minutes
2. 2
   Температураthe solution warmed slightly
3. 3
   workup.DISSOLUTIONall solids dissolved
4. 4
   Концентрированиеthe mixture was concentrated in vacuo
5. 5
   Другоеto remove ethanol
6. 6
   ДругоеThe gum obtained
7. 7
   Другоеwas partitioned between ethyl acetate and water
8. 8
   ЭкстракцияThe organic layer was extracted with saturated sodium bicarbonate solution (2×) and saturated sodium chloride solution
9. 9
   ДругоеDrying
10. 10
    Концентрирование(Na2SO4) and concentration in vacuo

Методика

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.

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