Imidazole → HCID 22161781, compound

HRID 1088795Notes

Reaction equation

HRID 1088795 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]([CH2:13][CH3:14])[CH2:10][CH2:9][C:8]2=[O:15].N1C=CN=C1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22].O>CN(C)C=O>[O:15]=[C:8]1[C:7]2[C:12](=[C:3]([CH2:2][O:1][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH:4]=[CH:5][CH:6]=2)[N:11]([CH2:13][CH3:14])[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 14685740HCID 14685740, compound

Product 1

HCID 22161781HCID 22161781, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Hydroxymethyl-1-ethyl-4-oxo-1,2,3,4-tetrahydroquinoline (1.44 g) was dissolved in dimethyl formamide (2 ml). Imidazole (1.57 g) and t-butyl dimethylsilyl chloride (1.16 g) were added to the solution and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate-toluene. After the extract was dried over anhydrous magnesium sulfate, the solvent was distilled off. The resulting residue was purified by silica gel column chromatography [eluent: n-hexane-ethyl acetate (3: 1) ] to give 4-oxo-8-t-butyldimethylsilyloxymethyl- 1-ethyl-1,2,3,4-tetrahydroquinoline (2.18 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate-toluene
  2. dry with materialAfter the extract was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off
  4. customThe resulting residue was purified by silica gel column chromatography [eluent: n-hexane-ethyl acetate (3: 1) ]

Sources & evidence

ORD record
ord-d659771ae40c41c18f2e9850374c8438
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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