3-(Trifluoromethyl)phenol → HCID 11386703, compound

HRID 1067659Notes

Reaction equation

HRID 1067659 reaction equation
[C:1]1([C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][OH:16])[N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:48][C:49]([F:58])([F:57])[C:50]1[CH:51]=[C:52](O)[CH:53]=[CH:54][CH:55]=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:23]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][O:16][C:55]3[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=3[C:49]([F:58])([F:57])[F:48])[N:10]=[CH:9]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 73763-(Trifluoromethyl)phenolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 108328403-(1-Trityl-1H-imidazol-4-YL)propan-1-OL

Product 1

HCID 11386703HCID 11386703, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

300 mg of 1-(triphenylmethyl)-4-(3-hydroxypropyl)-1H-imidazole (0.81 mmol) are dissolved in 8 ml of freshly distilled THF. 277 mg of triphenylphosphine (1.06 mmol) and 145 mg m-trifluoromethylphenol are added thereto, and the resulting mixture is cooled and stirred for 5 minutes under nitrogen. Diethyl azodicarboxylate (184 mg; 1.06 mmol), dissolved in freshly distilled THF (4 ml), is added gradually to the reaction mixture and while stirring continuously at room temperature for 12 hours. After removal of the solvent in vacuo, column chromatography (SiO2; first eluent: petroleum spirit; second eluent: petroleum spirit/diethyl ether (50:50)) performed on the crude reaction mixture gives a white powder which is reduced in petroleum ether to give an oil of 1-(triphenylmethyl)-4-[3-(trifluoromethylphenoxy)-propyl]-1H-imidazole. The latter (210 mg; 0.41 mmol) is heated at 70° C. for 3 hours in THF (5 ml) and 2N HCl (12 ml). The THF is removed under reduced pressure and Ph3COH is extracted with diethyl ether. The aqueous phase is neutralized with potassium carbonate and the product is extracted into diethyl ether or chloroform. This solution is dried and evaporated, giving an oil which is dissolved in 2-propanol. Oxalic acid (1.5 equivalents) is added and the abovementioned product (on addition of diethyl ether) in the form of the oxalate, m.p.: 204-208° C.

Workup

  1. temperaturethe resulting mixture is cooled
  2. additionis added gradually to the reaction mixture
  3. stirringwhile stirring continuously at room temperature for 12 hours
  4. customAfter removal of the solvent in vacuo, column chromatography (SiO2; first eluent: petroleum spirit; second eluent: petroleum spirit/diethyl ether (50:50))
  5. customreaction mixture
  6. customgives a white powder which

Sources & evidence

ORD record
ord-40f9fe3017ab4b9bb151661d69533ba9
Source dataset
uspto-grants-2001_06
Patent number
US06248765B1

Reaction notes

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