4-Nitrophenol → 2-(14-(4-Nitrophenoxy)-3,6,9,12-tetraoxatetradecyloxy)tetrahydro-2H-pyran

HRID 78710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 78710
CC1C=CC(S([O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+].[N+:39]([C:42]1[CH:47]=[CH:46][C:45](O)=[CH:44][CH:43]=1)([O-:41])=[O:40]>CN(C=O)C.O>[N+:39]([C:42]1[CH:47]=[CH:46][C:45]([O:11][CH2:12][CH2:13][O:14][CH2:15][CH2:16][O:17][CH2:18][CH2:19][O:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][O:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][O:28]2)=[CH:44][CH:43]=1)([O-:41])=[O:40]

Komponenten

6

Edukt 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 8670988714-((Tetrahydro-2H-pyran-2-yl)oxy)-3,6,9,12-tetraoxatetradecyl 4-methylbenzenesulfonate

Produkt 1

HCID 867098882-(14-(4-Nitrophenoxy)-3,6,9,12-tetraoxatetradecyloxy)tetrahydro-2H-pyran

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 27 (2.90 g, 6.09 mmol) in anhydrous DMF (11 mL) were added K2CO3 (2.53 g, 18.3 mmol) and 4-nitrophenol (0.847 g, 6.09 mmol), and the reaction mixture was heated to 80° C. for 16 h. After cooling, the reaction mixture was diluted in water, extracted three times with CH2Cl2, and then dried over MgSO4. The filtrate was concentrated under reduced pressure to give 28 as an oily residue (2.65 g, 98%): 1H NMR (300 MHz, CDCl3) δ 8.18 (d, J=9.2 Hz, 2H), 6.99 (d, J=9.2 Hz, 2H), 4.69-4.56 (m, 1H), 4.28-4.17 (m, 2H), 3.97-3.42 (m, 18H), 1.95-1.41 (m, 6H). 13C NMR (75 MHz, CDCl3) δ 163.82, 141.40, 125.75, 114.52, 98.83, 70.81, 70.51, 70.43, 69.27, 68.15, 66.54, 62.12, 30.48, 25.34, 19.41.

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted three times with CH2Cl2
  3. dry with materialdried over MgSO4
  4. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-187986b35c214013bf8b9e9acf5416d4
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841460B2

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