4-Chlorobenzophenone → 1-[(Benzyloxy)methyl]-alpha-(p-chlorophenyl)-alpha-phenylimidazole-2-methanol

HRID 261935

Reaktionsgleichung

Reaktionsgleichung von HRID 261935
[CH2:1]([O:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.[Cl:20][C:21]1[CH:34]=[CH:33][C:24]([C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:26])=[CH:23][CH:22]=1>CCCCCC.C(OCC)C.O1CCCC1>[CH2:1]([O:8][CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[C:11]1[C:25]([C:24]1[CH:23]=[CH:22][C:21]([Cl:20])=[CH:34][CH:33]=1)([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[OH:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 3

HCID 86534-ChlorobenzophenoneHCID 147959081-BenzyloxymethylimidazoleHCID 178418339Butyllithium

Produkt 1

HCID 124339151-[(Benzyloxy)methyl]-alpha-(p-chlorophenyl)-alpha-phenylimidazole-2-methanol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittel3×HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of 11.8 g. of 1-[(benzyloxy)methyl]imidazole in 100 ml. of anhydrous tetrahydrofuran and 50 ml. of anhydrous diethyl ether a solution of 38 ml. of a 20% butyllithium suspension in hexane dissolved in 75 ml. of anhydrous diethyl ether was added drop-wise with stirring at room temperature. Thereafter a solution of 14.6 g. of 4-chlorobenzophenone in 100 ml. of anhydrous tetrahydrofuran and 50 ml. of anhydrous diethyl ether was added drop-wise at room temperature. The mixture was kept for three hours and then extracted with a dilute acid solution. The acidic aqueous layer was made alkaline with 2 N sodium hydroxide solution and extracted with diethyl ether. Part of the ether was removed by evaporation and the residue washed with water. The ether solution was again concentrated and the desired compound crystallised from a mixture of toluene and petroleum ether (boiling range 28°-40° C.). Melting point of the product was 114.5°-117° C.

Aufarbeitung

  1. extractionextracted with a dilute acid solution
  2. extractionextracted with diethyl ether
  3. customPart of the ether was removed by evaporation
  4. washthe residue washed with water
  5. concentrationThe ether solution was again concentrated
  6. customthe desired compound crystallised from a mixture of toluene and petroleum ether (boiling range 28°-40° C.)
  7. customwas 114.5°-117° C.

Quellen und Nachweise

ORD-Eintrag
ord-39d68689ec82426b914e67b3c5e74115
Quelldatensatz
uspto-grants-1979_05
Patentnummer
US04152441

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