Imidazole → HCID 22995910, compound

HRID 1167194Notes

Reaction equation

HRID 1167194 reaction equation
[F:1][C:2]([F:22])([F:21])[S:3]([O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[C:10]([CH:17]([OH:20])[CH2:18][OH:19])[CH:11]=[CH:12][CH:13]=2)[N:8]=1)(=[O:5])=[O:4].N1C=CN=C1.[Si:28](Cl)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29].O>CN(C=O)C>[F:22][C:2]([F:1])([F:21])[S:3]([O:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[C:10]([CH:17]([OH:20])[CH2:18][O:19][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[CH:11]=[CH:12][CH:13]=2)[N:8]=1)(=[O:5])=[O:4]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 22995909HCID 22995909, compound

Product 1

HCID 22995910HCID 22995910, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 12 g (35 mmol) of 2-trifluoromethanesulfonyloxy-8-(1,2-dihydroxyethyl)quinoline, of 5.33 g (78.3 mmol) of imidazole and of 5.63 g of tert-butyldimethylsilyl chloride in 280 ml of DMF is stirred at ambient temperature for 16 h. 800 ml of water are added and extraction is carried out with ethyl acetate (3×250 ml). The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue is purified by silica chromatographic column (eluent: cyclohexane/ethyl acetate 8/2) to provide 13.8 g of 2-trifluoromethanesulfonyloxy-8-(1-hydroxy-2-tert-butyldimethylsilyloxyethyl)quinoline in the form of a yellow oil. (Yield: 91%)

Workup

  1. extractionextraction
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customThe residue is purified by silica chromatographic column (eluent: cyclohexane/ethyl acetate 8/2)

Sources & evidence

ORD record
ord-1656a92870ed44ceafb2eab874a363f9
Source dataset
uspto-grants-2003_09
Patent number
US06617336B1

Reaction notes

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