4-Iodo-1-tritylimidazole → 5-hydroxy-5-(1-trityl-1H-imidazol-4-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1095448Notes

Reaction equation

HRID 1095448 reaction equation
C([Mg]Cl)C.I[C:6]1[N:7]=[CH:8][N:9]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:10]=1.[O:30]=[C:31]1[CH2:40][CH2:39][CH2:38][C:37]2[CH:36]=[C:35]([C:41]#[N:42])[CH:34]=[CH:33][C:32]1=2>ClCCl>[OH:30][C:31]1([C:6]2[N:7]=[CH:8][N:9]([C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:10]=2)[CH2:40][CH2:39][CH2:38][C:37]2[CH:36]=[C:35]([C:41]#[N:42])[CH:34]=[CH:33][C:32]1=2

Participants

5

Reactant 3

HCID 6182524-Iodo-1-tritylimidazoleHCID 108991325-Oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrileHCID 178461633HCID 178461633, compound

Product 1

HCID 667819655-hydroxy-5-(1-trityl-1H-imidazol-4-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

12 mmol of ethylmagnesium chloride (3M in diethyl ether) are added to a solution of 10 mmol of 4-iodo-1-trityl-1H-imidazole [96797-15-8] in 40 ml of dichloromethane. The mixture is stirred for 45 minutes, and a solution of 10 mmol of 5-oxo-5,6,7,8-tetrahydronaphthalene-2-carbonitrile [90401-84-6] in 15 ml of dichloromethane is added. The reaction mixture is stirred at room temperature overnight and quenched with saturated ammonium chloride solution. The phases are separated, and the aqueous phase is extracted with dichloromethane (3×). The combined organic phases are washed with brine, dried with sodium sulphate and evaporated. The title compound is identified from the residue on the basis of the Rf by flash chromatography (SiO2 60F).

Workup

  1. stirringThe reaction mixture is stirred at room temperature overnight
  2. customquenched with saturated ammonium chloride solution
  3. customThe phases are separated
  4. extractionthe aqueous phase is extracted with dichloromethane (3×)
  5. washThe combined organic phases are washed with brine
  6. dry with materialdried with sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-4add305c0e194f7192bd792305f89e81
Source dataset
uspto-grants-2012_03
Patent number
US08138179B2

Reaction notes

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