4-Fluorophenol → 1-triphenylmethyl-4-[3-(4-fluorophenoxy)propyl]-1H-imidazole

HRID 744079Notes

Reaction equation

HRID 744079 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:28]1([C:34]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)([C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[N:35]2[CH:39]=[C:38]([CH2:40][CH2:41][CH2:42]O)[N:37]=[CH:36]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:50]1([C:34]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:44]2[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=2)[N:35]2[CH:39]=[C:38]([CH2:40][CH2:41][CH2:42][O:8][C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[N:37]=[CH:36]2)[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

6

Reactant 4

HCID 97324-FluorophenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 108328403-(1-Trityl-1H-imidazol-4-YL)propan-1-OL

Product 1

HCID 106001421-triphenylmethyl-4-[3-(4-fluorophenoxy)propyl]-1H-imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5 ml of freshly distilled tetrahydrofuran, 120 mg (1 mmol) of 4-fluorophenol and 270 mg (1 mmol) of triphenylphosphine are added, under nitrogen, to 368 mg (1 mmol) of 1-triphenylmethyl-4-(3-hydroxypropyl)-1H-imidazole. The resulting mixture is cooled and stirred for 5 min. 180 mg (1 mmol) of diethyl azodicarboxylate in 5 ml of tetrahydrofuran are then slowly added. Stirring is continued at room temperature for 3 days under nitrogen. The solvent is then evaporated under reduced pressure and the residue is subjected to chromatography on a column of silica gel, using diethyl ether as eluent, to give 1-triphenylmethyl-4-[3-(4-fluorophenoxy)propyl]-1H-imidazole.

Workup

  1. temperatureThe resulting mixture is cooled
  2. stirringStirring
  3. waitis continued at room temperature for 3 days under nitrogen
  4. customThe solvent is then evaporated under reduced pressure

Sources & evidence

ORD record
ord-947fcf1973a749e4b2ce81c382925eb5
Source dataset
uspto-grants-1996_09
Patent number
US05559113

Reaction notes

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