Reaction #83163

Reaction equation

3-aminopropyltriethoxysilane

triethylamine

acryloyl chloride

→

liquid

Yield 77.0%

3-(Triethoxysilyl)propylacrylamide

Yield 77.0%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.ADDITIONAfter completion of addition the reaction mixture
3. 3
   Filtrationfiltered
4. 4
   ConcentrationThe filtrate was concentrated to an oil
5. 5
   workup.ADDITIONdiluted with hexane (100 mL)
6. 6
   Filtrationfiltered
7. 7
   ConcentrationThe resulting filtrate was concentrated to oil
8. 8
   workup.DISTILLATIONdistilled in vacuo

Procedure

To a solution of acryloyl chloride (8.5 mL, 105 mmol) in dry dichloromethane (250 mL) cooled to 0° C. was added dropwise a mixture of 3-aminopropyltriethoxysilane (23.5 mL, 100 mmol) and triethylamine (13.9 mL, 100 mmol) in dichloromethane (50 mL). After completion of addition the reaction mixture was stirred for 30 min, then filtered. The filtrate was concentrated to an oil, diluted with hexane (100 mL) and filtered. The resulting filtrate was concentrated to oil and distilled in vacuo. The product was obtained as a viscous liquid (21.2 g, 77%), b.p. 142-145/1 mm Hg.

Source