Reaktion #321848

Reaktionsgleichung

cyclopropylmagnesium bromide

5H-dibenzo[a,d]cyclohepten-5-one

ammonium chloride

→

5-cyclopropyl-5H-dibenzo[a,d]cyclohepten-5-ol

Lösungsmittel

water

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwhen addition
2. 2
   Temperaturwas heated
3. 3
   Temperaturat reflux for 30 minutes
4. 4
   TemperaturThe reaction mixture was cooled on an ice-bath
5. 5
   Extraktionextracted with diethyl ether (2×50 ml)
6. 6
   WaschenThe combined organic extracts were washed with water
7. 7
   Trocknendried (Na2SO4)
8. 8
   Sonstigethe solvent was evaporated in vacuo

Vorschrift

A solution of cyclopropylmagnesium bromide in dry THF (prepared from cyclopropylbromide (8.0 g, 0.067 mol), magnesium turnings (1.3 g, 0.053 mol) and dry THF (35 ml)) was placed under an atmosphere of nitrogen. A solution of 5H-dibenzo[a,d]cyclohepten-5-one (6.0 g, 0.028 mol) in dry THF (15 ml) was added dropwise and when addition was complete the mixture was heated at reflux for 30 minutes. The reaction mixture was cooled on an ice-bath and saturated ammonium chloride (35 ml) was carefully added. The mixture was diluted with water (50 ml) and extracted with diethyl ether (2×50 ml). The combined organic extracts were washed with water, dried (Na2SO4) and the solvent was evaporated in vacuo to give 8.6 g of crude 5-cyclopropyl-5H-dibenzo[a,d]cyclohepten-5-ol.

Quelle