4-Iodo-1-tritylimidazole → HCID 10717796, compound

HRID 1290232Notes

Reaction equation

HRID 1290232 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[C:32]([CH:36]=[O:37])=[CH:33][S:34][CH:35]=1>C(Cl)Cl>[CH3:30][C:31]1[C:32]([CH:36]([C:23]2[N:22]=[CH:21][N:20]([C:1]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:24]=2)[OH:37])=[CH:33][S:34][CH:35]=1

Participants

5

Reactant 3

HCID 6182524-Iodo-1-tritylimidazoleHCID 8188974-methylthiophene-3-carbaldehydeHCID 178461630HCID 178461630, compound

Product 1

HCID 10717796HCID 10717796, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-trityl-4-iodo-imidazole (11.8 g, 27 mmol) in dry CH2Cl2 (75 mL) was added EtMgBr (10.0 mL, 3.0M in Et2O), and the solution was stirred for 3 hrs. Then a solution of 4-methylthiophene-3-carboxaldehyde (3.3 g, 27 mmol) in CH2Cl2 (25 mL) was added. The reaction mixture was stirred at room temperature overnight and then was 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 washed with a small portion of water, dried (Na2SO4), 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 with charcoal treatment from EtOAc to give (4-methylthien-3-yl)-1-trityl-imidazol-4-yl-methanol, B2. 1H NMR (CDCl3) supported the assigned structure. ##STR39##

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. customwas quenched with aqueous NH4Cl
  3. customThe mixture was transferred to a separatory funnel
  4. extractionthe aqueous layer was extracted with a second portion of CH2Cl2
  5. washThe combined extracts were washed with a small portion of water
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customThe solvent was evaporated in vacuo
  9. customto give a thick syrup which
  10. customwas triturated with Et2O
  11. customto give a solid which
  12. customwas recrystallized with charcoal treatment from EtOAc

Sources & evidence

ORD record
ord-90929995a5ce41008d1359175f9d0b59
Source dataset
uspto-grants-1998_05
Patent number
US05750720

Reaction notes

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