4-Iodo-1-tritylimidazole → HCID 10696020, compound

HRID 1290237Notes

Reaction equation

HRID 1290237 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-].[CH2:30]([C:32]1[S:33][C:34]([CH2:39][CH3:40])=[CH:35][C:36]=1[CH:37]=[O:38])[CH3:31]>C(Cl)Cl.ClCl>[CH2:30]([C:32]1[S:33][C:34]([CH2:39][CH3:40])=[CH:35][C:36]=1[CH:37]([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:38])[CH3:31]

Participants

6

Reactant 3

HCID 6182524-Iodo-1-tritylimidazoleHCID 18923847HCID 18923847, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 10696020HCID 10696020, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24526ChlorineSolvent

Procedure

To a solution of N-trityl-4-iodo-imidazole (13.5 g, 31 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 2,5-diethylthiophene-3-carboxaldehyde, D6, (5.0 g, 30 mmol) in CH2 Cl2 (20 mL) was added, and the reaction mixture was stirred at room temperature overnight. The reaction was quenched with NH4Cl (aq) and the mixture was transferred to a separatory funnel. The aqueous layer was extracted with a second portion of CH2Cl2. The extracts were combined and washed with a small portion of water, dried (Na2 SO4), 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 EtOAc to give (2,5-diethylthien-3-yl)-1-trityl-imidazol-4-yl-methanol, E6. 1H NMR (CDCl3) supported the assigned structure. ##STR52##

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customThe reaction was quenched with NH4Cl (aq)
  3. customthe mixture was transferred to a separatory funnel
  4. extractionThe aqueous layer was extracted with a second portion of CH2Cl2
  5. washwashed with a small portion of water
  6. customdried (Na2 SO4)
  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 from EtOAc

Sources & evidence

ORD record
ord-62733fa619834aa0869ca69b3a3fd43d
Source dataset
uspto-grants-1998_05
Patent number
US05750720

Reaction notes

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