Reaktion #1359

Reaktionsgleichung

sodium boron hydride

4-bromo-2-i-butyl-1-indanone

→

desired product

Ausbeute 96.4%

4-bromo-2-i-butyl-1-hydroxyindane

Ausbeute 96.4%

Lösungsmittel

ethanol

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 300-ml three-necked round flask equipped with a stirring bar
2. 2
   workup.ADDITIONTo the mixture was added dropwise a solution
3. 3
   workup.ADDITIONAfter the addition
4. 4
   EinengenThen, the reaction mixture was concentrated under reduced pressure, which
5. 5
   Extraktionwas then extracted with 150 ml of water and 150 ml of ether
6. 6
   SonstigeThe organic phase was separated
7. 7
   Extraktionthe aqueous phase was further extracted with 100 ml of ether
8. 8
   WaschenThe combined organic phase was washed with 100 ml of a saturated NaCl aq. two times
9. 9
   Trocknenby dried over anhydrous Na2SO4
10. 10
    SonstigeThe solvent was evaporated under reduced pressure

Vorschrift

A 300-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a dropping funnel and a thermometer was charged with 2.51 g (66.3 mmol) of sodium boron hydride and 85 ml of ethanol. To the mixture was added dropwise a solution containing 37.0 g (132.6 mmol) of the above-obtained 4-bromo-2-i-butyl-1-indanone dissolved in 55 ml of ethanol at room temperature under a nitrogen atmosphere. After the addition was completed, the mixture was further stirred for 16 hours. Then, the reaction mixture was concentrated under reduced pressure, which was then extracted with 150 ml of water and 150 ml of ether. The organic phase was separated, and the aqueous phase was further extracted with 100 ml of ether. The combined organic phase was washed with 100 ml of a saturated NaCl aq. two times, followed by dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure to obtain 34.4 g of the desired product (mixture of two isomers) as a pale yellow solid (yield: 96%). This alcohol was used in the next reaction without further purification.

Quelle