Reaktionsgleichung
Br[CH2:2][C:3]1([CH3:7])[CH2:6][O:5][CH2:4]1.[F:8][C:9]([F:29])([C:13]([F:28])([F:27])[C:14]([F:26])([F:25])[C:15]([F:24])([F:23])[C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])[CH2:10][CH2:11][OH:12].[H-].[Na+]>CN(C)C=O>[F:8][C:9]([F:29])([C:13]([F:27])([F:28])[C:14]([F:25])([F:26])[C:15]([F:23])([F:24])[C:16]([F:21])([F:22])[C:17]([F:20])([F:19])[F:18])[CH2:10][CH2:11][O:12][CH2:2][C:3]1([CH3:7])[CH2:6][O:5][CH2:4]1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
In a manner similar to that described above, 12.0 grams of 3-bromomethyl-3-methyloxetane (73 mmol) was reacted with 26.5 grams of 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctan-1-ol (72.7 mmol) in 300 milliliters of dimethylformamide in the presence of 3.9 grams of a 50 weight percent dispersion of sodium hydride (81 mmol) in mineral oil at 85° C. for 24 hours to give 21.5 grams (70% yield) of 3-(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyloxymethyl)-3-methyloxetane, a colorless oil with a boiling point of 66°-68° C./2-2.5 mm-Hg; 1H NMR (CDCl3) δ4.50 and 4.36 (AB, J=5.5 Hz, 4H), 3.78 (t, J=6.6 Hz, 2H), 3.53 (s, 2H), 2.42 (triplet of triplets, J=6.6 and 18 Hz, 2H), and 1.31 (s, 3H); 13C NMR (CDCl3) δ79.89, 78.30, 63.31, 39.9, 31.64 (t), and 21.1 (signals due to carbons bearing fluorines are not included due to the complex splitting patterns and low peak intensities); 19F NMR δ-81.4 (3F), -113.8 (2F), -118.2 (2F), -112.3 (2F), -124.1 (2F) and -126.7 (2F). The elemental analysis was: Calculated for C13H13F13O2 : C, 34.8; H, 2.9; F, 55.1. Found: C, 35.1; H, 3.0; F, 54.7.
Quellen und Nachweise
- ORD-Eintrag
- ord-9c93143e3fef47a380bb2738d02b3908
- Quelldatensatz
- uspto-grants-1997_09
- Patentnummer
- US05668251
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