Hexachlorobutadiene → 1,4-Bis(dimethylaminodimethylsilyl)butadiyne

Temperature

-78 °C

A flame dried 250 ml Schlenk flask containing THF (20 ml) was cooled to −78° C. and n-butyl lithium (20 ml of 2.4 M in hexane, 48.0 mmol) was added by syringe. After several minutes hexachlorobutadiene (1.88 ml, 12.0 mmol) was added dropwise via syringe over a 10 minute period. After completion of addition, the cold bath was removed and the mixture stirred at room temperature for 3 hours. The resulting 1,4-dilithio-1,3-butadiyne was used without further purification. The flask was then recooled to −78° C., and dimethylaminodimethylchlorosilane (3.6 ml, 24 mmol) was added by syringe. The flask was removed from the cold bath and the reaction mixture stirred at room temperature for 16 hours. At this time 1H NMR analysis indicated complete disappearance of dimethylaminodimethylchlorosilane and formation of 1,4-bis-(dimethylaminodimethylsilyl)-butadiyne. The THF was removed in vacuo, and the mixture was taken up in a minimum amount of pentane and filtered. The pentane was removed in vacuo to give 2.91 g (96%) of 1,4-bis(dimethylaminodimethylsilyl)butadiyne.

1. customA flame dried 250 ml Schlenk flask
2. additioncontaining THF (20 ml)
3. additionAfter completion of addition
4. customthe cold bath was removed
5. customThe resulting 1,4-dilithio-1,3-butadiyne was used without further purification
6. customwas then recooled to −78° C.
7. customThe flask was removed from the cold bath
8. stirringthe reaction mixture stirred at room temperature for 16 hours
9. customThe THF was removed in vacuo
10. filtrationfiltered
11. customThe pentane was removed in vacuo

ORD record

ord-70bbbe2b6f1f459f9a5280efe6554373

Source dataset

uspto-grants-2003_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06579955B2