Diethyl Ether → ST51008769

HRID 227210

Reaction equation

HRID 227210 reaction equation
CCOCC.Br[C:7]1[S:8][CH:9]=[CH:10][CH:11]=1.[Li]CCCC.[CH3:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=[CH:20][CH:19]=1>[Cl-].[Na+].O>[CH3:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=[C:20]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)[CH:19]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 102854-MethylquinolineHCID 138512-BromothiopheneHCID 178418339Butyllithium

Product 1

HCID 2366884ST51008769Yield 65%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A two necked round-bottom flask (250 mL) containing a stir bar fitted with a reflux condenser was evacuated and purged with nitrogen gas. Dry ether (50 mL) and 2-bromothiophene (0.0191 mol, 3.06 g) was added to the flask followed by the slow addition of n-BuLi (0.0229 mol, 9.17 mL) via a syringe pump. The reaction mixture was stirred at room temperature for 30 min to 40 min and then 4-methylquinoline (0.0191 mol, 2.72 g) was slowly added. The reaction mixture was refluxed for an additional 2 to 3 hr. The reaction mixture was then cooled to room temperature and diluted with an aqueous brine solution and extracted with ether (3×30 mL). The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography using hexanes/CH2Cl2 as eluent to afford 2.77 g of 4-methyl-(2-thiophenyl)quinoline (65% yield).

Workup

  1. additionA two necked round-bottom flask (250 mL) containing a stir bar
  2. customfitted with a reflux condenser
  3. customwas evacuated
  4. custompurged with nitrogen gas
  5. temperatureThe reaction mixture was refluxed for an additional 2 to 3 hr
  6. temperatureThe reaction mixture was then cooled to room temperature
  7. extractionextracted with ether (3×30 mL)
  8. dry with materialThe combined extracts were dried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8f433c8298c540b7841bb436909ec25d
Source dataset
uspto-grants-2009_07
Patent number
US07560176B2

Linked notes

Loading…