Triphenylphosphine → 1-triphenylmethyl-4-[2-(4-trifluoromethylphenoxy)ethyl]-1H-imidazole

HRID 726262Notes

Reaction equation

HRID 726262 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:31]1([C:37]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[N:38]2[CH:42]=[C:41]([CH2:43][CH2:44]O)[N:40]=[CH:39]2)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:52]1([C:37]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[N:38]2[CH:42]=[C:41]([CH2:43][CH2:44][O:9][C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:10])([F:11])[F:1])=[CH:8][CH:7]=3)[N:40]=[CH:39]2)[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 678744-(Trifluoromethyl)phenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 106894902-(1-Trityl-1H-imidazol-4-yl)ethanol

Product 1

HCID 107439231-triphenylmethyl-4-[2-(4-trifluoromethylphenoxy)ethyl]-1H-imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

15 ml of freshly distilled tetrahydrofuran, 340 mg (2.1 mmol) of 4-trifluoromethylphenol and 550 mg (2.1 mmol) of triphenylphosphine are added under nitrogen to 708 g (2 mmol) of 1-triphenylmethyl-4-(2-hydroxyethyl)-1H-imidazole. The resulting mixture is cooled and stirred for 5 min. 66 mg (2.1 mmol) of diethyl azodicarboxylate in 10 ml of tetrahydrofuran are then slowly added. Stirring is continued at room temperature for 2 hours under nitrogen. The solvent is then evaporated under reduced pressure and the residue is chromatographed on a column of silica gel, using diethyl ether as the eluent, to give 1-triphenylmethyl-4-[2-(4-trifluoromethylphenoxy)ethyl]-1H-imidazole.

Workup

  1. temperatureThe resulting mixture is cooled
  2. stirringStirring
  3. waitis continued at room temperature for 2 hours under nitrogen
  4. customThe solvent is then evaporated under reduced pressure
  5. customthe residue is chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-0dfce220ff9a426b98460ce0ad7ecc98
Source dataset
uspto-grants-1998_01
Patent number
US05708171

Reaction notes

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