Reaktion #321846

Reaktionsgleichung

hydrochloric acid

cyclopropylmagnesium bromide

10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one

ammonium chloride

→

5-cyclopropyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol

Lösungsmittel

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 (2×200 ml)
6. 6
   TrocknenThe combined organic extracts were dried (Na2SO4)
7. 7
   Sonstigethe solvent was evaporated in vacuo

Vorschrift

A solution of cyclopropylmagnesium bromide in dry THF (prepared from cyclopropylbromide (12.1 g, 0.10 mol), magnesium turnings (2.45 g, 0.10 mol) and dry THF (65 ml)) was placed under an atmosphere of nitrogen. A solution of 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-one (10.4 g, 0.05 mol) in dry THF (25 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 (50 ml) was carefully added. The mixture was neutralized with 2N hydrochloric acid and extracted with diethyl ether (2×200 ml). The combined organic extracts were dried (Na2SO4) and the solvent was evaporated in vacuo to give 13.1 g of crude 5-cyclopropyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ol.

Quelle