1-(triphenylmethyl)-1H-imidazole-4-carbaldehyde → HCID 54381600, Verbindung

HRID 264096

Reaktionsgleichung

Reaktionsgleichung von HRID 264096
[Li]CCCC.[Br-].[CH2:7]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[C:37]1([C:43]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[N:44]2[CH:48]=[C:47]([CH:49]=O)[N:46]=[CH:45]2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>C1COCC1>[CH:49]([C:47]1[N:46]=[CH:45][N:44]([C:43]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)([C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:48]=1)=[CH:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH3:7]

Komponenten

5

Edukt 3

HCID 6182331-(triphenylmethyl)-1H-imidazole-4-carbaldehydeHCID 3085198Triphenylundecylphosphonium bromideHCID 178418339Butyllithium

Produkt 1

HCID 54381600HCID 54381600, VerbindungAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of n-BuLi (4.1 mL, 6.5 mmol, 1.6M in hexanes) was added dropwise to a suspension of n-undecyl-triphenylphosphoniumbromide (3.09 g, 6.2 mmol, obtained from triphenylphosphine and undecylbromide) in 100 mL THF at -78° C. under an atmosphere of N2. The resulting orange solution was stirred for 45 minutes before a solution of 1-(triphenylmethyl)-4-imidazolecarboxaldehyde (2.0 g, 5.9 mmol, Ref: Kelly J. L., Miller C. A., and McLean E. W., J. Med. Chem. 1977;20:721) in 75 mL THF was added dropwise. Warmed to room temperature and stirred for 16 hours. Quenched by adding 50 mL saturated NH4Cl solution and concentrating in vacuo. The residue was partitioned between water and dichloromethane. The organic layer was dried over MgSO4, filtered, and concentrated to give a yellow oil. Chromatography (10% EtOAc/hexanes on silica) gave the title compound (1.8 g, 64%) as a clear oil.

Aufarbeitung

  1. customQuenched
  2. additionby adding 50 mL saturated NH4Cl solution
  3. concentrationconcentrating in vacuo
  4. customThe residue was partitioned between water and dichloromethane
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-bb721834dec940dab7e70644d02dbd7e
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646170

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