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Imidazole → 2-phenyl-3-methyl-8-(1-(S)-hydroxy-2-[tert-butyldimethylsilyloxy]ethyl)quinoline

HRID 1167181
Notes
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Reaction equation

HRID 1167181 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[C:14]1([C:20]2[C:29]([CH3:30])=[CH:28][C:27]3[C:22](=[C:23]([C@H:31]([OH:34])[CH2:32][OH:33])[CH:24]=[CH:25][CH:26]=3)[N:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C)C=O>[C:14]1([C:20]2[C:29]([CH3:30])=[CH:28][C:27]3[C:22](=[C:23]([C@H:31]([OH:34])[CH2:32][O:33][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:24]=[CH:25][CH:26]=3)[N:21]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 213565432-phenyl-3-methyl-8-(1-(S),2-dihydroxyethyl)quinoline

Product 1

HCID 213565442-phenyl-3-methyl-8-(1-(S)-hydroxy-2-[tert-butyldimethylsilyloxy]ethyl)quinolineYield 92%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

3.7 g (24.3 mmol) of tert-butyldimethylsilyl chloride and 3.4 g of (50 mmol) of imidazole are added at ambient temperature to a solution of 6.5 g (23.2 mmol) of 2-phenyl-3-methyl-8-(1-(S),2-dihydroxyethyl)-quinoline in 200 ml of dimethylformamide. The reaction medium is stirred for 16 hours. After addition of 200 ml of distilled water, the reaction mixture is extracted with 3×200 ml of ethyl acetate. The organic phases are combined, washed with 300 ml of distilled water, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue is purified by silica gel chromatography (eluent: ethyl acetate/cyclohexane to provide 8.4 g of 2-phenyl-3-methyl-8-(1-(S)-hydroxy-2-[tert-butyldimethylsilyloxy]ethyl)quinoline in the form of a colorless oil. (Yield: 85%)

Workup

  1. extractionthe reaction mixture is extracted with 3×200 ml of ethyl acetate
  2. washwashed with 300 ml of distilled water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue is purified by silica gel chromatography (eluent

Sources & evidence

ORD record
ord-4da1e5de9ba44f47ab078b4dd1d361bb
Source dataset
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06617336B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes