Reaction #64920

Reaction equation

2-(4-chlorophenyl)ethyl methanesulfonate

t-butylsulfonylacetonitrile

→

orange oil

Yield 80.3%

4-(4-chlorophenyl)-2-(t-butylsulfonyl)butanenitrile

Yield 80.3%

Solvents

DMF

DMF

Conditions

Workup

1. 1
   Washof 60% sodium hydride (NaH), which had been previously washed two times with successive 30 mL portions of hexane
2. 2
   workup.ADDITIONwas added dropwise
3. 3
   workup.STIRRINGThe mixture was stirred at room temperature for 3 hrs
4. 4
   Otheran additional 96 hrs
5. 5
   workup.STIRRINGThe mixture was stirred yet an additional 96 hrs at room temperature after which analysis by gas liquid phase chromatography (GLC)
6. 6
   OtherThe reaction was quenched by the addition of 100 mL of diethyl ether and 50 mL of water
7. 7
   WashThe ether was washed with water
8. 8
   Extractionthe combined aqueous phases were extracted with 50 mL of ethyl acetate
9. 9
   Dryingdried with sodium sulfate
10. 10
    Filtrationfiltered
11. 11
    Concentrationconcentrated

Procedure

Into a 3-neck, 200 milliliter (mL) round bottom flask was charged 2.4 grams (g), 0.06 mole, of 60% sodium hydride (NaH), which had been previously washed two times with successive 30 mL portions of hexane, in 30 mL of dimethylformamide (DMF). While stirring under nitrogen, 7.6 g (0.05 mole) of t-butylsulfonylacetonitrile in 25 mL of DMF was added. The mixture was stirred for 0.5 hour (hr) and 12.8 g (0.055 mole) of 2-(4-chlorophenyl)ethyl methanesulfonate in 25 mL of DMF was added dropwise. The mixture was stirred at room temperature for 3 hrs. and then an additional 96 hrs by which time the mixture had changed to an orange slurry. The mixture was stirred yet an additional 96 hrs at room temperature after which analysis by gas liquid phase chromatography (GLC) indicated the absence of starting material. The reaction was quenched by the addition of 100 mL of diethyl ether and 50 mL of water. The ether was washed with water and the combined aqueous phases were extracted with 50 mL of ethyl acetate. The organic phases were combined, dried with sodium sulfate, filtered and concentrated to give 12.0 g of an orange oil (80.3% yield) which was used directly in the next step.

Source