Chlorodimethylphenylsilane → HCID 131723247, compound

HRID 2185070Notes

Reaction equation

C([Li])CCC.[CH3:6][C:7]1[CH2:11][C:10]([CH3:12])=[C:9]([CH3:13])[C:8]=1[CH3:14].Cl[Si:16]([CH3:24])([CH3:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[CH3:23][Si:16]([CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:7]1([CH3:6])[CH:11]=[C:10]([CH3:12])[C:9]([CH3:13])=[C:8]1[CH3:14]

Participants

Conditions

Temperature: 25 °C

Procedure

30 ml (48 mmol) of n-butyllithium (1.6 M in hexane) were added dropwise at −78° C. to a solution of 5.4 g (44.2 mmol) of tetramethylcyclopentadiene in 90 ml of THF over the course of about 20 minutes. The mixture was then stirred at 25° C. for 24 hours. The solution was then cooled again to −78° C., 8.3 g (48.6 mmol) of chlorodimethylphenylsilane were added dropwise over the course of 15 minutes, and the mixture was stirred at 25° C. for 24 hours. The THF was then removed under reduced pressure, and the residue was taken up in 50 ml of pentane. The insoluble precipitate was filtered off and the pentane was removed under reduced pressure. The yellow liquid residue was distilled under a high vacuum. The product boils at 83 to 85° C. Characterization was carried out by means of 1H-NMR spectroscopy.

Workup

temperatureThe solution was then cooled again to −78° C.
stirringthe mixture was stirred at 25° C. for 24 hours
customThe THF was then removed under reduced pressure
filtrationThe insoluble precipitate was filtered off
customthe pentane was removed under reduced pressure
distillationThe yellow liquid residue was distilled under a high vacuum

Sources & evidence

ORD record: ord-58d337e79f66424896fd45c24c0d7997
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06399727B1

Reaction notes

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