4-Nitrophenol → 2-(17-(4-Nitrophenoxy)-3,6,9,12,15-pentaoxaheptadecyloxy)tetrahydro-2H-pyran

Reaktionsgleichung

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][CH2:27][CH2:28][O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)(=O)=O)=CC=1.C([O-])([O-])=O.[K+].[K+].[N+:42]([C:45]1[CH:50]=[CH:49][C:48](O)=[CH:47][CH:46]=1)([O-:44])=[O:43]>CN(C=O)C.O>[N+:42]([C:45]1[CH:50]=[CH:49][C:48]([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][CH2:27][CH2:28][O:29][CH:30]2[CH2:35][CH2:34][CH2:33][CH2:32][O:31]2)=[CH:47][CH:46]=1)([O-:44])=[O:43]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a stirred solution of 34 (7.03 g, 13.5 mmol) in anhydrous DMF (24 mL) were added K2CO3 (5.60 g, 40.5 mmol), and 4-nitrophenol (1.88 g, 13.5 mmol). The reaction mixture was heated to 80° C. for 16 h. Upon completion, 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 an oily residue, which provided 35 as a yellow oil without further purification (6.30 g, 96%): 1H NMR (300 MHz, CDCl3) δ 8.19 (d, J=9.3 Hz, 2H), 6.97 (d, J=9.3 Hz, 2H), 4.67-4.57 (m, 1H), 4.26-4.17 (m, 2H), 3.95-3.79 (m, 2H), 3.78-3.34 (m, 22H), 1.47-1.84 (m, 6H).

Aufarbeitung

extractionextracted three times with CH2Cl2
dry with materialdried over MgSO4
concentrationThe filtrate was concentrated under reduced pressure
customto give an oily residue, which

Quellen und Nachweise

ORD-Eintrag: ord-f0f871ae4c964a0e85d59b4a07ae8edd
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08841460B2

Notizen zur Reaktion

Wird geladen…