Imidazole → HCID 57046043, compound

HRID 1780233Notes

Reaction equation

HRID 1780233 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[C@@H:14]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C@@H:13]([OH:20])[C@@H:12]([OH:21])[CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].CN(C=[O:39])C>>[Si:27]([O:21][C@@H:12]1[C@@H:13]([OH:20])[C@H:14]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])[C:10]([CH2:9][O:8][C:1](=[O:39])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:11]1)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]

Participants

5

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 11011791HCID 11011791, compound

Product 1

HCID 57046043HCID 57046043, compound

Procedure

A solution of 25 (8.04 g, 27.5 mmol) and imidazole (7.05 g, 103.55 mmol) in anhydrous DMF (80 ml) was treated with tert-butyldimethylsilyl chloride (6.70 g, 44.45 mmol). The mixture was stirred at room temperature under a blanket of argon for 40 min and quenched by the addition of water (100 ml). The reaction mixture was extracted with ethyl acetate (3×100 ml), and the combined organic extract was washed with brine (2×100 ml) and dried over Na2SO4. The solvent was evaporated and the product purified by flash column chromatography over silica gel to give 9.77 g (87.4%) of pure 26 as an oil. Analysis calculated for C23H38O4Si.0.5 H2O: C, 66.46; H, 9.46. Found: C, 66.41; H, 9.31.

Workup

  1. customquenched by the addition of water (100 ml)
  2. extractionThe reaction mixture was extracted with ethyl acetate (3×100 ml)
  3. extractionthe combined organic extract
  4. washwas washed with brine (2×100 ml)
  5. dry with materialdried over Na2SO4
  6. customThe solvent was evaporated
  7. customthe product purified by flash column chromatography over silica gel

Sources & evidence

ORD record
ord-ac67fba21ca74a4393a5eb0c13f83da9
Source dataset
uspto-grants-1997_05
Patent number
US05629454

Reaction notes

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