Reaktion #1059902

Reaktionsgleichung

1-[3-(dimethylamino)-propyl]-indene

sodium hydroxide

hydrogen peroxide

borane

hydrochloric acid

→

oil

Ausbeute 81.0%

trans-1-[3-(Dimethylamino)propyl]-2-indanol

Ausbeute 81.0%

Lösungsmittel

water

tetrahydrofuran

tetrahydrofuran

water

water

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeis coold to 0° under nitrogen
2. 2
   Temperaturis cooled to 0°
3. 3
   workup.ADDITIONthe following added in the given order
4. 4
   Extraktionextracted with chloroform (3 × 400 ml)
5. 5
   Sonstigeto give a white solid which
6. 6
   Sonstigeis collected
7. 7
   TemperaturThe residue is cooled
8. 8
   Extraktionextracted with chloroform (200 ml, discard)
9. 9
   Extraktionextracted with chloroform (3 × 300 ml)
10. 10
    SonstigeDrying
11. 11
    Sonstigesolvent removal

Vorschrift

A solution of 20.6 g (0.10 mole) of 1-[3-(dimethylamino)-propyl]-indene in 100 ml of tetrahydrofuran is coold to 0° under nitrogen and 200 ml of 1M borane in tetrahydrofuran added over 30 minutes. After stirring overnight at ambient temperature the solution is cooled to 0° and the following added in the given order: 30 ml of water added cautiously, 170 ml of 10% sodium hydroxide solution and 32 ml of 30% hydrogen peroxide solution. After 1 hour at 0° the mixture is diluted with 1 liter of water and extracted with chloroform (3 × 400 ml) to give a white solid which is refluxed with 300 ml each of ethanol and 5% hydrochloric acid for 1 hour. After addition of 300 ml of water, 400 ml of distillate is collected. The residue is cooled, extracted with chloroform (200 ml, discard), basified with excess sodium hydroxide and extracted with chloroform (3 × 300 ml). Drying and solvent removal give 17.6 g of oil (81%, 1 spot on TLC).

Quelle