Water → HCID 67388542, compound

Participants

Reaction Steps

(Pyrrole-TEOS) To a 500 mL 3-neck round bottom flask equipped with a stirbar was added 30.8 g (10× the amount of water generated by the reaction by weight) of 5 Å molecular sieves. The flask was then equipped with a reflux condenser and the remaining necks were sealed with rubber septa. The reaction flask was evacuated and backfilled with dry nitrogen three times. After the final backfill cycle, 18.9 g (85.4 mmol) of 3-aminopropyltriethoxysilane was added to the flask, along with 40 mL of anhydrous toluene. With rapid stirring, 10.8 mL (89.7 mmol) of 2,5-hexanedione was added dropwise via syringe. The contents were heated to reflux and stirred under nitrogen overnight. After an overnight stir, the contents were filtered. The filtrate was filtered a second time and collected. The collected filtrate was concentrated via rotary evaporation to yield an orange liquid (23.7 g, 94%). This solid was isolated in >98% purity, as characterized by 1H NMR spectroscopy and was not purified further. 1H NMR (CDCl3, 400 MHz): 0.65 (m, 2H); 1.23 (m, 9H); 1.75 (m, 2H); 2.23 (s, 6H) 3.77 (m, 2H); 3.84 (m, 6H); 5.76 (s, 2H). 13C NMR (CDCl3, 100 MHz): 7.64; 12.43; 18.26; 24.38; 45.99; 58.42; 104.91; 127.28.

Provenance & Evidence