Tetrahydrofuran → HCID 19881174, compound

HRID 847356Notes

Reaction equation

HRID 847356 reaction equation
C1COCC1.Br[C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[N:13]=[CH:12][CH:11]=[CH:10]2.C([Li])CCC.[CH2:22]([Sn:26](Cl)([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25]>CCCCC.CCOCC>[N:13]1[C:14]2[C:9](=[CH:8][C:7]([Sn:26]([CH2:27][CH2:28][CH2:29][CH3:30])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:22][CH2:23][CH2:24][CH3:25])=[CH:16][CH:15]=2)[CH:10]=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 15096Tributyltin ChlorideHCID 792436-BromoquinolineHCID 178418339Butyllithium

Product 1

HCID 19881174HCID 19881174, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolvent

Procedure

To 250 mL of THF was added 14 g (67 mmol) of 6-bromoquinoline and 44 mL (88 mmol) of 2M butyllithium in pentane was added at -70° under argon. The reaction was stirred for 15 minutes and 28.4 g (87.2 mmol) of tributyltin chloride was added at such a rate that the temperature remained below -60° . When addition was complete, the mixture was allowed to warm to -50° at which point the dark orange color characteristic of the anion became light amber. The mixture was stirred for 14 hrs at -70° and poured into ice-water and ether. The layers were separated, the ether layer washed with water, dried with magnesium sulfate, filtered and concentrated. The resultant oil was chromatographed on a silica gel column (30 cm ×6 cm) using 30% ether in hexane to provide 17.8 g (63%) of 6-quinolinyltributylstannane.

Workup

  1. additionwas added at -70° under argon
  2. customremained below -60°
  3. additionWhen addition
  4. temperatureto warm to -50° at which point the dark orange color characteristic of the anion
  5. stirringThe mixture was stirred for 14 hrs at -70°
  6. customThe layers were separated
  7. washthe ether layer washed with water
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe resultant oil was chromatographed on a silica gel column (30 cm ×6 cm)

Sources & evidence

ORD record
ord-a17eacada33d4884b5884c9c2f630f2a
Source dataset
uspto-grants-1992_08
Patent number
US05141931

Reaction notes

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