4-Iodo-1-tritylimidazole → HCID 10694859, compound

HRID 1290239Notes

Reaction equation

HRID 1290239 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.C[Mg+].[Br-].[CH2:29]([C:31]1[S:32][CH:33]=[CH:34][C:35]=1[CH:36]=[O:37])[CH3:30]>C(Cl)Cl.C(OCC)C.ClCl>[CH2:29]([C:31]1[S:32][CH:33]=[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])[CH3:30]

Participants

7

Reactant 3

HCID 6182524-Iodo-1-tritylimidazoleHCID 64307213-Thiophenecarboxaldehyde, 2-ethyl- (9CI)HCID 178418689HCID 178418689, compound

Product 1

HCID 10694859HCID 10694859, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 24526ChlorineSolvent

Procedure

To a solution of N-trityl-4-iodo-imidazole (4.1 g, 0.0095 mol) in dry CH2Cl2 (75 mL) was added a solution of MeMgBr (4.0 mL, 3.0M) in diethyl ether and the solution was stirred for 3 hrs. Then a solution of 2-ethylthiophene-3-carboxaldehyde, B7, (1.66 g, 0.0087 mol) in CH2 Cl2 (20 mL) was added and the reaction mixture was stirred at room temperature overnight. The reaction was quenched with aqueous NH4Cl 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, and the residue was triturated with Et2O to give (2-ethylthien-3-yl)-1-trityl-imidazol-4-yl-methanol, C7, as a beige solid which was taken on to the next step directly. ##STR56##

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. customThe reaction was 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. washwashed with a small portion of water
  6. customdried (Na2 SO4)
  7. filtrationfiltered
  8. customThe solvent was evaporated in vacuo
  9. customthe residue was triturated with Et2O

Sources & evidence

ORD record
ord-57a83d1e28104053b28c7911cbbb5145
Source dataset
uspto-grants-1998_05
Patent number
US05750720

Reaction notes

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