Water → HCID 66974263, compound

HRID 499837Notes

Reaction equation

HRID 499837 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13](OCC)=[O:14])[N:10]=[C:9]2[S:18][CH3:19])=[CH:4][CH:3]=1.[Li+].[BH4-].O.CCOC(C)=O>C1COCC1>[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([CH2:13][OH:14])[N:10]=[C:9]2[S:18][CH3:19])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4148881Lithium borohydrideHCID 66974213HCID 66974213, compound

Product 1

HCID 66974263HCID 66974263, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 1-(4-iodophenyl)-2-(methylthio)-1H-imidazole-4-carboxylate (0.49 g, 1.26 mmol) in anhydrous THF (10 mL) at room temperature, LiBH4 (2M in THF, 3.2 mL, 6.4 mmol) was added. The mixture was stirred at room temperature overnight. H2O and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give (1-(4-iodophenyl)-2-(methylthio)-1H-imidazol-4-yl)methanol (0.41 g).

Workup

  1. customThe organic phase was separated
  2. washwashed with 5% NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34d1f1b0e01a4785af7280f6f1bf2391
Source dataset
uspto-grants-2010_08
Patent number
US07767697B2

Reaction notes

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