Tetrahydrofuran → [2-(tri-n-Butylstannyl)-1-ethynyl]cyclobutane

HRID 412159Notes

Reaction equation

HRID 412159 reaction equation
[Li]CCCC.[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].O1CCCC1.ClCCCCC#C.[CH2:24]([Sn:28](Cl)([CH2:33][CH2:34][CH2:35][CH3:36])[CH2:29][CH2:30][CH2:31][CH3:32])[CH2:25][CH2:26][CH3:27]>CCCCCC>[CH2:33]([Sn:28]([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:29][CH2:30][CH2:31][CH3:32])[C:6]#[C:7][CH:8]1[CH2:11][CH2:10][CH2:9]1)[CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 15096Tributyltin ChlorideHCID 2720016-Chloro-1-hexyneHCID 178418244HCID 178418244, compound

Product 1

HCID 70009182[2-(tri-n-Butylstannyl)-1-ethynyl]cyclobutane

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a solution of n-BuLi/hexane (7.28 mL, 18.2 mmol, 2.5 M) at −5° C. was added tetrahydrofuran dropwise, maintaining the temperature below +9° C. 6-Chloro-1-hexyne (1.00 mL, 8.92 mmol) was added at +5° C., and the solution was stirred for six hours. The reaction was quenched by the addition of tri-n-butyltin chloride (2.66 mL, 9.81 mmol), and was allowed to stir for an additional 10 minutes. The solution was poured into hexane, washed with saturated NaHCO3 solution and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The product was isolated as a colorless liquid which was used without further purification.

Workup

  1. temperaturemaintaining the temperature below +9° C
  2. stirringto stir for an additional 10 minutes
  3. washwashed with saturated NaHCO3 solution and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was isolated as a colorless liquid which
  8. customwas used without further purification

Sources & evidence

ORD record
ord-85d1daba82b2440eb10a838f518e3d4d
Source dataset
uspto-grants-2003_05
Patent number
US06562823B1

Reaction notes

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