Water → HCID 67388542, compound

(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.

1. customgenerated by the reaction by weight) of 5 Å molecular sieves
2. customThe flask was then equipped with a reflux condenser
3. customthe remaining necks were sealed with rubber septa
4. customThe reaction flask was evacuated
5. temperatureThe contents were heated
6. temperatureto reflux
7. stirringAfter an overnight stir
8. filtrationthe contents were filtered
9. filtrationThe filtrate was filtered a second time
10. customcollected
11. concentrationThe collected filtrate was concentrated via rotary evaporation

ORD record

ord-8b8b0f85ce174d78bb15ea8ae763b86e

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08022159B2