Sodium Iodide → 3-[2-[2-(2-Ethoxyethoxy)ethoxy]ethoxy]-5-(octadecyloxy)benzoic acid phenylmethyl ester
Reaktionsgleichung
[C:1]1([CH2:7][O:8][C:9](=[O:36])[C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]=[C:12]([OH:35])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:37]([O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47]Br)[CH3:38].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[C:1]1([CH2:7][O:8][C:9](=[O:36])[C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]=[C:12]([O:35][CH2:47][CH2:46][O:45][CH2:44][CH2:43][O:42][CH2:41][CH2:40][O:39][CH2:37][CH3:38])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Komponenten
7
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A mixture of 2 g (4 mmol) of 3-hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester, 3.65 g (15.8 mmol) of 2-[2-(2-ethoxyethoxy)ethoxy]ethyl bromide, 1.2 g (8 mmol) of sodium iodide and 2.2 g (16 mmol) of potassium carbonate in 60 ml of acetone and 30 ml of DMF was stirred at reflux for 40 hours. The usual workup followed by chromatography of the crude product on 200 g of silica gel using 40% ethyl acetate-hexane gave 1.76 g of 3-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]-5-(octadecyloxy)benzoic acid phenylmethyl ester as an oil. The nmr and mass spectra were compatible with the structure.
Aufarbeitung
- temperatureat reflux for 40 hours
Quellen und Nachweise
- ORD-Eintrag
- ord-cb56a5f6c8d84f578e9e332ee1b8b605
- Quelldatensatz
- uspto-grants-1994_03
- Patentnummer
- US05298652
Notizen zur Reaktion
Wird geladen…