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4-Iodobenzonitrile → 4-[2-(1-trityl-1H-imidazol-4-ylmethoxy)acetyl]benzonitrile

HRID 1360136
Notes
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Reaction equation

HRID 1360136 reaction equation
I[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH:10]([Mg]Cl)([CH3:12])[CH3:11].CON(C)[C:18](=[O:46])[CH2:19][O:20][CH2:21][C:22]1[N:23]=[CH:24][N:25]([C:27](C2C=CC=CC=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)C2C=CC=CC=2)[CH:26]=1>O1CCCC1>[C:27]([N:25]1[CH:26]=[C:22]([CH2:21][O:20][CH2:19][C:18]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[O:46])[N:23]=[CH:24]1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:10]1[CH:12]=[CH:26][CH:22]=[CH:21][CH:11]=1)[C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 764674-IodobenzonitrileHCID 86632953N-methoxy-N-methyl-2-(1-trityl-1H-imidazol-4-ylmethoxy)acetamideHCID 178418918HCID 178418918, compound

Product 1

HCID 667823264-[2-(1-trityl-1H-imidazol-4-ylmethoxy)acetyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-30 °C

Procedure

A solution of 14 mmol of 4-iodobenzonitrile [3058-39-7] in 20 ml of tetrahydrofuran is cooled to −30° C., and 14.80 mmol of i-propylmagnesium chloride (2M in tetrahydrofuran) are added. The mixture is stirred at −30° C. for 60 minutes and a solution, precooled to −30° C., of 10.0 mmol of N-methoxy-N-methyl-2-(1-trityl-1H-imidazol-4-ylmethoxy)acetamide in 30 ml of tetrahydrofuran is added. The mixture is stirred at −30° C. for 30 minutes, and then the reaction mixture is warmed to room temperature and quenched with saturated aqueous ammonium chloride, solution. The phases are separated, and the aqueous phase is extracted with ethyl acetate (3×). The combined organic phases are washed with brine, dried with magnesium sulphate and evaporated. The title compound is identified from the residue on the basis of the Rf by flash chromatography (SiO2 60F).

Workup

  1. additionis added
  2. stirringThe mixture is stirred at −30° C. for 30 minutes
  3. temperaturethe reaction mixture is warmed to room temperature
  4. customquenched with saturated aqueous ammonium chloride, solution
  5. customThe phases are separated
  6. extractionthe aqueous phase is extracted with ethyl acetate (3×)
  7. washThe combined organic phases are washed with brine
  8. dry with materialdried with magnesium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-c3e962acbe3745babacef3a6a7070b29
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07879847B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes