Chlorotrifluoroethylene → 1,2,2-Trifluoroethenyl-triethylsilane

HRID 1979622Notes

Reaction equation

N#N.CCCCC.Cl[C:9]([F:13])=[C:10]([F:12])[F:11].Cl[Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:16][CH3:17].CCCCCC.C([Li])CCC>CCCCC.C(OCC)C.O1CCCC1>[CH2:16]([Si:15]([CH2:20][CH3:21])([CH2:18][CH3:19])[C:9]([F:13])=[C:10]([F:12])[F:11])[CH3:17]

Participants

Conditions

Temperature: -130 °C

Procedure

A reactor flushed with argon was cooled with a liquid nitrogen-pentane cooling medium, and 15.0 g (0.129 mol) of chlorotrifluoroetylene was fed into the reactor. To this reactor, 50 ml of anhydrous tetrahydrofuran (THF), 30 ml of diethyl ether (Et2O) and 30 ml of pentane were introduced to bring the concentration of chlorotrifluoroethylene to 1 mmol/ml. Then, 16.1 g (0.107 mol) of chlorotriethylsilane was introduced. The reactor was cooled to -130° C., and then 88 ml (0.140 mol) of a hexane solution of butyllithium (1.6M) was introduced over a period of one hour. Then, the temperature was gradually raised to room temperature over 7.5 hours. The reaction solution was filtered and dried through a column of Celite placed on anhydrous sodium sulfate. The solvent was removed, and the residue was distilled, whereby 17.8 g of triethyltrifluorovinylsilane was obtained as a colorless transparent oil (yield: 85.1%).

Workup

customA reactor flushed with argon
temperatureThen, the temperature was gradually raised to room temperature over 7.5 hours
filtrationThe reaction solution was filtered
customdried through a column of Celite
customThe solvent was removed
distillationthe residue was distilled

Sources & evidence

ORD record: ord-9917910f829e46d888517bdbeb80d796
Source dataset: uspto-grants-1984_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04481366

Reaction notes

Loading…