4-Iodo-1-tritylimidazole → (2,5-Dimethylthien-3-yl)-1-trityl-imidazol-4-yl-methanol

HRID 1290235Notes

Reaction equation

HRID 1290235 reaction equation
[C:1]([N:20]1[CH:24]=[C:23](I)[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[Mg+].[Br-].[CH3:30][C:31]1[S:32][C:33]([CH3:38])=[CH:34][C:35]=1[CH:36]=[O:37]>C(Cl)Cl>[CH3:30][C:31]1[S:32][C:33]([CH3:38])=[CH:34][C:35]=1[CH:36]([C:23]1[N:22]=[CH:21][N:20]([C:1]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:24]=1)[OH:37]

Participants

5

Reactant 3

HCID 6182524-Iodo-1-tritylimidazoleHCID 27627592,5-Dimethylthiophene-3-carbaldehydeHCID 178461630HCID 178461630, compound

Product 1

HCID 11797817(2,5-Dimethylthien-3-yl)-1-trityl-imidazol-4-yl-methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-trityl-4-iodo-imidazole (11.8 g, 27 mmol) in dry CH2Cl2 (200 mL) was added EtMgBr (11.0 mL, 3.0M in Et2O). After complete halogen-metal exchange this solution was cannulated into a solution of 2,5-dimethylthiophene-3-carboxaldehyde (3.5 g, 25 mmol) in 50 mL of CH2Cl2. The reaction mixture was stirred at room temperature for 1 hr and then quenched with aqueous NH4Cl. The mixture was transferred to a separatory funnel and the aqueous layer was extracted with a second portion of CH2Cl2. The combined extracts were dried (MgSO4) and filtered. The solvent was evaporated in vacuo to give a thick syrup which was triturated with Et2O to give a solid which was recrystallized from acetone to give (2,5-dimethylthien-3-yl)-1-trityl-imidazol-4-yl-methanol, A5. 1H NMR (CDCl3) supported the assigned structure. ##STR46##

Workup

  1. customquenched with aqueous NH4Cl
  2. customThe mixture was transferred to a separatory funnel
  3. extractionthe aqueous layer was extracted with a second portion of CH2Cl2
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customThe solvent was evaporated in vacuo
  7. customto give a thick syrup which
  8. customwas triturated with Et2O
  9. customto give a solid which
  10. customwas recrystallized from acetone

Sources & evidence

ORD record
ord-5bbb2d5563db4932ba55d1d1d650adbb
Source dataset
uspto-grants-1998_05
Patent number
US05750720

Reaction notes

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