Water → HCID 23445033, compound

HRID 397898Notes

Reaction equation

HRID 397898 reaction equation
[I:1][C:2]1[N:3]=[C:4]([CH:15]=[O:16])[N:5]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=1.[BH4-].[Na+].O>C(O)C>[I:1][C:2]1[N:3]=[C:4]([CH2:15][OH:16])[N:5]([CH2:7][O:8][CH2:9][CH2:10][Si:11]([CH3:12])([CH3:13])[CH3:14])[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 11131912HCID 11131912, compound

Product 1

HCID 23445033HCID 23445033, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carbaldehyde (4.6 g, 13.1 mmol) was dissolved in ethanol (50 ml) under argon. Sodium borohydride (0.514 g, 13.1 mmol) was added and the mixture was stirred at room temperature for 45 min. H2O (200 ml) was added. The aqueous layer was extracted 3 times with AcOEt. The combined extracts were dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude residue was taken up in hexane and stirred at rt. Filtration provided [4-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazol-2-yl]-methanol (4.0 g, 87%) as a white solid. MS: m/e=354.0 (M+).

Workup

  1. extractionThe aqueous layer was extracted 3 times with AcOEt
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. stirringstirred at rt
  6. filtrationFiltration

Sources & evidence

ORD record
ord-a8dfbea2a04d41c18bf937d3361139bb
Source dataset
uspto-grants-2003_08
Patent number
US06610723B2

Reaction notes

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