Methanol → HCID 178443526, Verbindung

HRID 1376373Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1376373
[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-9f3bb0bdc52e4e6b897970dab476235d
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05663053

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