Bis(2-ethylhexyl)amine → 3,3,3-Trifluoropropyl bis(2-ethylhexyl)aminodimethoxysilane

Temperature

15 °C

3,3,3-Trifluoropropyl(bis(2-ethylhexyl)aminodimethoxysilane--A 500 mL round bottomed flask was charged with tetrahydrofuran (300 mL) and isopropylmagnesium chloride (25 mL of a 2.0 M solution in THF, 50 mmol). The contents were cooled to 15° C. Bis(2-ethylhexyl)amine (50 mmol) was added over fifteen minutes via pressure equalizing addition funnel. The cold bath was removed and the contents stirred for two hours. 3,3,3-Trifluoropropyltrimethoxysilane (45 mmol) was added via pressure equalizing addition funnel. The contents were brought to reflux (65-70° C.) for two hours, and reaction progress was monitored by GC. Isolation was accomplished by removing the THF via rotary evaporation, taking the residue up in ether (250 mL), filtration and ether removal via rotary evaporation. Purification was accomplished by distillation to provide 3,3,3-trifluoropropyl bis(2-ethylhexyl)aminodimethoxysilane (44 mmol; 98% yield). C21H44NO2SiF3 (mw=427.66) bp=200° C. at 1.4 mmHg; 1H NMR: (CDCl3) δ 3.5 (s, 6H), 2.6-2.4 (dd, 4H), 2.2-2.0 (m, 2H), 1.6-1.1 (m, 18H), 1.0-0.7 (m, 14H); 13C NMR: (CDCl3) δ 128 (quartet, J=275 Hz), 50.4, 48.5, 39.4, 36.9, 30.8, 29.1, 28.2 (quartet, J=30 Hz), 23.2, 14.2, 10.3, 3.2; MS: m/z (relative abundance) 328 (100), 230 (25.6), 155 (7.4), 109 (2.9).

1. additionaddition funnel
2. customThe cold bath was removed
3. additionaddition funnel
4. temperatureto reflux (65-70° C.) for two hours
5. customreaction progress
6. customby removing the THF
7. customvia rotary evaporation
8. filtrationup in ether (250 mL), filtration and ether removal
9. customvia rotary evaporation
10. customPurification
11. distillationwas accomplished by distillation

ORD record

ord-01b6999923c54c6dbe7f38602d9dab81

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06130180