Reaction #40920

Reaction equation

ammonium chloride

4-fluorophenyl magnesium bromide

aminonitrile

Dimethylamino-(1,4-dioxa-spiro[4.5]dec-8-yl)-acetonitrile

water

→

(1,4-dioxa-spiro[4.5]dec-8-yl-4-fluorophenylmethyl]-dimethylamine

Solvents

THF

THF

Conditions

Workup

1. 1
   workup.ADDITIONwere added
2. 2
   Temperaturewhile cooling with ice
3. 3
   Extractionthe mixture was extracted with diethyl ether (3×100 ml)
4. 4
   WashThe organic phase was washed with water and saturated sodium chloride solution
5. 5
   Dryingdried (Na2SO4)
6. 6
   Concentrationconcentrated by evaporation

Procedure

A solution of the aminonitrile 6 (19.89 g 88 mmole) in absolute THF (160 ml) was added dropwise under argon and cooling with ice to a 1M solution of 4-fluorophenyl magnesium bromide in THF (220 ml, 220 mmole) and stirred for 20 hours at RT. To work up the reaction mixture, saturated ammonium chloride solution (100 ml) and water (100 ml) were added while cooling with ice, and the mixture was extracted with diethyl ether (3×100 ml). The organic phase was washed with water and saturated sodium chloride solution, dried (Na2SO4) and concentrated by evaporation.

Source