Chlorotrimethylsilane → HCID 21848599, compound

Participants

Reaction Steps

Recrystallized 2,5-bis(2',2',3',3',4',4',4'-heptafluoro-1'-hydroxybutyl)pyrrole (0.5 mmol, 0.2316 g) was dissolved in 25 ml of dry THF and transferred to a cooled (0° C.) suspension of sodium hydride (1.0 mmol, 0.024 g) in 60 mL of THF. When hydrogen evolution ceased (after 1 hour) trimethylsilyl chloride (1 mmol, 0.109 g) was added by syringe. The mixture became cloudy and was stirred at room temperature for 1 hour before the solvent was removed in vacuo. The remaining residue was partitioned between 10% sodium bicarbonate solution and pentane. The organic layer was washed twice with water and dried over magnesium sulfate, filtered and evaporated to leave a colorless oil (0.204 g, 0.34 mmol, 67%). 1H NMR (CDCl3, 360 MHz) 8.68 (broad s, 1 H); 6.15 (d, 2 H, J=2.7 Hz); 5.13 (dd, 2 H, J1-18.8 Hz, J2=5.0 Hz); 0.03 (s, 18 H).

Provenance & Evidence