Reaction #1379894

Reaction equation

water

Acryloyl chloride

dichloromethane

hydroxylamine

N-Methyl,N-(tert-butyldiphenylsilyl)hydroxylamine

dichloromethane

→

N-Methyl,N-(tert-butyldiphenylsilyloxy)acrylamide

Conditions

Workup

1. 1
   workup.ADDITIONN,Ndiisopropylethylamine was added
2. 2
   Otherthe two layers were separated
3. 3
   WashThe organic layer was washed with 10% ammonium chloride, saturated bicarbonate solution, and brine
4. 4
   DryingThe organic solution was then dried with magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Otherthe solvent evaporated under reduced pressure
7. 7
   OtherThe crude product was purified by flash chromatography (silica gel)
8. 8
   workup.ADDITIONa mixture of hexane and ethyl acetate
9. 9
   Washto elute the compound
10. 10
    OtherThe purification

Procedure

Dry dichloromethane (50 mL) was added to N-Methyl,N-(tert-butyldiphenylsilyl)hydroxylamine to dissolve the hydroxylamine derivative. N,Ndiisopropylethylamine was added. The resulting solution was stirred and cooled at 0° C. with an ice bath. Acryloyl chloride in 10 mL of dry dichloromethane was added. Then water was added and the two layers were separated. The organic layer was washed with 10% ammonium chloride, saturated bicarbonate solution, and brine. The organic solution was then dried with magnesium sulfate, filtered, and the solvent evaporated under reduced pressure. The crude product was purified by flash chromatography (silica gel) using a mixture of hexane and ethyl acetate to elute the compound. The purification produced N-Methyl,N-(tert-butyldiphenylsilyloxy)acrylamide (28).

Source