2-methylthiophene-3-carbaldehyde → HCID 10526927, compound

HRID 1290230Notes

Reaction equation

HRID 1290230 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][CH:33]=[CH:34][C:35]=1[CH:36]=[O:37]>C(Cl)Cl>[CH3:30][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]

Participants

5

Reactant 3

HCID 5293982-methylthiophene-3-carbaldehydeHCID 6182524-Iodo-1-tritylimidazoleHCID 178461630HCID 178461630, compound

Product 1

HCID 10526927HCID 10526927, 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 2-methylthiophene-3-carboxaldehyde (3.3 g, 27 mmol) in CH2Cl2 (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 (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 (2-methylthien-3-yl)-1-trityl-imidazol-4-yl-methanol, B1. 1H NMR (CDCl3) supported the assigned structure. ##STR36##

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. 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-6ff6bc4e397d412e8909cdc1bff22a95
Source dataset
uspto-grants-1998_05
Patent number
US05750720

Reaction notes

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