Pentane → HCID 19437716, compound

HRID 1886703Notes

Reaction equation

HRID 1886703 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][C:12]([CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])=[CH:13][C:8]=3[O:7][C:6]=2[CH:23]=1.C([Li])(C)(C)C.CCCCC.[CH3:34][Sn:35](Cl)([CH3:37])[CH3:36]>C1COCC1.C(Cl)Cl.CCOCC>[CH3:34][Sn:35]([CH3:37])([CH3:36])[C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][C:12]([CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])=[CH:13][C:8]=3[O:7][C:6]=2[CH:23]=1

Participants

8

Reactant 4

HCID 8003PentaneHCID 14016Trimethyltin chlorideHCID 19432448HCID 19432448, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 19437716HCID 19437716, compoundYield 68.6%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the dibenzofuran 4 (995 mg, 2.5 mmol) in anhydrous THF (25 mL) at -78° C. under a nitrogen atmosphere was added a 1.5M t-butyllithium in pentane solution (3.0 mL, 5.25 mmol). The resulting yellow solution was stirred for 100 min., then trimethyltin chloride (548 mg, 2.75 mmol) was added as a solid. The mixture was allowed to warm to ambient temperature and then stirred for 3 hours. The reaction mixture was then poured into ether and the organic solution was washed with water (3 times) and then with brine. The organic solution was then dried with magnesium sulfate, filtered and concentrated under vacuum. Flash chromatography of the residue (silica gel, 10% methylene chloride in hexanes) provided 815 mg of the stannane 23 (68% yield) as a crystalline solid.

Workup

  1. stirringstirred for 3 hours
  2. washthe organic solution was washed with water (3 times)
  3. dry with materialThe organic solution was then dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-e3910dfe393e42a09b90a23330b61da1
Source dataset
uspto-grants-1992_09
Patent number
US05151512

Reaction notes

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