Methanol → HCID 178443526, Verbindung

HRID 265401

Reaktionsgleichung

Reaktionsgleichung von HRID 265401
[C:1]1([N:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]=[C:8]2[O:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:33][P:34]([O:38]CC)[O:35][CH2:36][CH3:37].CO.O>C1(C)C=CC=CC=1>[CH2:36]([CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][O:24][C:8]1[N:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:9]=1)[CH3:37].[CH3:33][PH:34](=[O:35])[O-:38]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 85063Diethyl methylphosphoniteHCID 229164121,4,5-Triphenyl-2-(7-bromoheptyloxy)imidazole

Produkt 1

HCID 178443526HCID 178443526, VerbindungAusbeute 57,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 1,4,5-triphenyl-2-(7-bromoheptyloxy)-imidazole (1.75 g) and diethyl methylphosphonite (2.45 g) in toluene (10 ml) was heated at reflux temperature for 48 hours. Methanol and water were added and the mixture evaporated to an oil. This was chromatographed on silica gel (ethyl acetate/ethanol). The resulting oil slowly crystallised and was triturated with ether/petroleum ether, filtered then recrystallised from ethanol/ether to give ethyl 7-(1,4,5-triphenyl-imidazol-2-yloxy)heptane-methylphosphinate (1.06 g, 57%) as a white solid, m.p. 101°-2° C. Found: C, 72.05; H, 7.26; N, 5.52%; C31H37N2O3P; Requires: C, 72.07; H, 7.22; N, 5.42%.

Aufarbeitung

  1. temperatureat reflux temperature for 48 hours
  2. customthe mixture evaporated to an oil
  3. customThis was chromatographed on silica gel (ethyl acetate/ethanol)
  4. customThe resulting oil slowly crystallised
  5. customwas triturated with ether/petroleum ether
  6. filtrationfiltered
  7. customthen recrystallised from ethanol/ether

Quellen und Nachweise

ORD-Eintrag
ord-b4e6be7428ea45bfb31e2b127adfab45
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05648373

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