Dimethylformamide → HCID 11131912, compound

HRID 397899Notes

Reaction equation

HRID 397899 reaction equation
[I:1][C:2]1[N:3]=[CH:4][N:5]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1I.C([Li])CCC.CN([CH:24]=[O:25])C.[NH4+].[Cl-]>C1COCC1>[I:1][C:2]1[N:3]=[C:4]([CH:24]=[O:25])[N:5]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 11091612HCID 11091612, compoundHCID 178418339Butyllithium

Product 1

HCID 11131912HCID 11131912, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-45 °C

Procedure

A solution of 4,5-diiodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (8.86 g, 19.68 mmol) in anhydrous THF (110 ml) under argon was cooled to −78° C. and was treated dropwise with n-butyllithium (13.5 ml, 21.65 mmol, 1.6M in hexane). After 10 minutes stirring at −78° C. and 30 minutes at −45° C., the reaction mixture was cooled to −78° C. and treated at once with DMF (10 ml). The mixture was allowed to warm to room temperature and saturated NH4Cl (150 ml) was added. The aqueous layer was extracted 2 times with AcOEt. The combined extracts were dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was chromatographed (silica, elution with hexane/AcOEt=98:2) to provide the title compound (5.18 g, 75%) as a light yellow oil. MS: m/e 352.1 (M+).

Workup

  1. temperaturethe reaction mixture was cooled to −78° C.
  2. temperatureto warm to room temperature
  3. extractionThe aqueous layer was extracted 2 times with AcOEt
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe residue was chromatographed
  8. wash(silica, elution with hexane/AcOEt=98:2)

Sources & evidence

ORD record
ord-98c7a63332304349b42d56185772423b
Source dataset
uspto-grants-2003_08
Patent number
US06610723B2

Reaction notes

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