Triphenylphosphine → 1-triphenylmethyl-4-[3-(4-trifluoromethylphenoxy)propyl]-1H-imidazole

HRID 726274Notes

Reaction equation

HRID 726274 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:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[N:38]2[CH:42]=[C:41]([CH2:43][CH2:44][CH2:45]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:53]1([C:37]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)([C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[N:38]2[CH:42]=[C:41]([CH2:43][CH2:44][CH2:45][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:58]=[CH:57][CH:56]=[CH:55][CH:54]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 678744-(Trifluoromethyl)phenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 108328403-(1-Trityl-1H-imidazol-4-YL)propan-1-OL

Product 1

HCID 108394731-triphenylmethyl-4-[3-(4-trifluoromethylphenoxy)propyl]-1H-imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5 ml of tetrahydrofuran, 129 mg (0.8 mmol) of 4-trifluoromethylphenol and 209 mg (0.8mmol) of triphenylphosphine are added, under nitrogen, to 280 mg (0.76 mmol) of 1-triphenylmethyl-4-(3-hydroxypropyl)-1H-imidazole. The resulting mixture is stirred for 5 min. 139 mg (0.8 mmol) of diethyl azodicarboxylate in 5 ml of tetrahydrofuran are then slowly added. Stirring is continued at room temperature for 3 hours under nitrogen. The solvent is then evaporated and the residue is then chromatographed on a column of silica gel (first eluent petroleum ether containing increasing amounts of diethyl ether up to 100%) to give the monohydrate of 1-triphenylmethyl-4-[3-(4-trifluoromethylphenoxy)propyl]-1H-imidazole which is crystallized from ethanol, M.p.: 150°-151° C.

Workup

  1. stirringStirring
  2. waitis continued at room temperature for 3 hours under nitrogen
  3. customThe solvent is then evaporated
  4. customthe residue is then chromatographed on a column of silica gel (first eluent petroleum ether containing increasing amounts of diethyl ether up to 100%)

Sources & evidence

ORD record
ord-49ec3416d84d410190f75ee6cf99e004
Source dataset
uspto-grants-1998_01
Patent number
US05708171

Reaction notes

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