Tetrabutylammonium Fluoride → (5-((2-(2-(2-Methoxyethoxy)ethoxy)ethyl)(2-methyl-2-(methyldisulfanyl)propyl)amino)-1,3-phenylene)dimethanol

HRID 336326Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 336326
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][CH2:27][C:28]1[CH:29]=[C:30]([CH:49]=[C:50]([CH2:52][O:53][Si](C(C)(C)C)(C)C)[CH:51]=1)[N:31]([CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][O:47][CH3:48])[CH2:32][C:33]([CH3:38])([S:35][S:36][CH3:37])[CH3:34])(C(C)(C)C)(C)C>C1COCC1>[CH3:48][O:47][CH2:46][CH2:45][O:44][CH2:43][CH2:42][O:41][CH2:40][CH2:39][N:31]([CH2:32][C:33]([CH3:38])([S:35][S:36][CH3:37])[CH3:34])[C:30]1[CH:29]=[C:28]([CH2:27][OH:26])[CH:51]=[C:50]([CH2:52][OH:53])[CH:49]=1

Komponenten

4

Edukt 2

HCID 2724141Tetrabutylammonium FluorideHCID 866712843,5-bis(((tert-butyldimethylsilyl)oxy)methyl)-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-N-(2-methyl-2-(methyldisulfanyl)propyl)aniline

Produkt 1

HCID 86671285(5-((2-(2-(2-Methoxyethoxy)ethoxy)ethyl)(2-methyl-2-(methyldisulfanyl)propyl)amino)-1,3-phenylene)dimethanolAusbeute 87,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Tetrabutylammonium fluoride (1M in THF) (10.57 ml, 10.57 mmol) was added dropwise to stirring solution of 3,5-bis(((tert-butyldimethylsilyl)oxy)methyl)-N-(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-N-(2-methyl-2-(methyldisulfanyl)propyl)aniline (3.5 g, 5.29 mmol) in anhydrous THF (65 ml) at 0° C. in an ice bath. Following addition the mixture was stirred at ambient temperature for two hours. The mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate. The extracts were washed with water and brine, dried with magnesium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography (MeOH/DCM) yielded (5-((2-(2-(2-methoxyethoxy)ethoxy)ethyl)(2-methyl-2-(methyldisulfanyl)propyl)amino)-1,3-phenylene)dimethanol (2 g, 87%). 1H NMR (400 Hz, CDCl3): δ 6.76 (s, 2H), 6.63 (s, 1H), 4.55 (s, 4H), 3.65-3.51 (m, 14H), 3.35 (s, 3H), 2.44 (s, 3H), 1.33 (s, 6H); 13C NMR (400 Hz, CDCl3): δ 149.0, 142.35, 114.0, 111.1, 71.98, 70.7, 70.6, 70.5, 67.6, 65.5, 59.75, 59.1, 53.9, 51.9, 26.6, 25.7, 20.75; MS (m/z). found 456.2 (M+Na)+. See FIG. 46.

Aufarbeitung

  1. additionaddition the mixture
  2. customThe mixture was quenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  4. washThe extracts were washed with water and brine
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by silica gel chromatography (MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-3975e18fb11d431481c2c3a78d6f3bdc
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889669B2

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