Reacción #648596

Ecuación de reacción

cyclopropylmagnesium bromide

5-fluoro-1-indanone

diethyl ether

→

title compound

1-Cyclopropyl-5-fluoro-2,3-dihydro-1H-inden-1-ol

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThe reaction mixture was added to a saturated, ice-cold aqueous ammonium chloride solution
2. 2
   Otrothe phases were separated
3. 3
   Extracciónthe aqueous phase was extracted with dichloromethane
4. 4
   Secadothe combined organic phases were dried over magnesium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated
7. 7
   OtroThe residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient)

Procedimiento

2.00 g (13.3 mmol) of 5-fluoro-1-indanone were introduced into 50 ml of diethyl ether at RT, 40 ml (20.0 mmol) of a 0.5N solution of cyclopropylmagnesium bromide in tetrahydrofuran were added, and the mixture was stirred at RT overnight. The reaction mixture was added to a saturated, ice-cold aqueous ammonium chloride solution, the phases were separated, the aqueous phase was extracted with dichloromethane, and the combined organic phases were dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography on silica gel (mobile phase: toluene/ethyl acetate gradient) to result in 2.22 g (87% of theory) of the title compound which were reacted without further purification.

Fuente