Tributyltin Chloride → HCID 11057369, compound

HRID 2306199Notes

Reaction equation

HRID 2306199 reaction equation
C([Li])CCC.Cl[CH2:7][CH2:8][CH2:9][C:10]#[CH:11].[CH2:12]([Sn:16](Cl)([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH3:15].C([O-])(O)=O.[Na+]>CCCCCC.C1COCC1>[CH2:21]([Sn:16]([CH2:12][CH2:13][CH2:14][CH3:15])([CH2:17][CH2:18][CH2:19][CH3:20])[C:7]#[C:8][CH:9]1[CH2:11][CH2:10]1)[CH2:22][CH2:23][CH3:24]

Participants

7

Reactant 4

HCID 15096Tributyltin ChlorideHCID 843081-Pentyne, 5-chloro-HCID 516892Sodium BicarbonateHCID 178418339Butyllithium

Product 1

HCID 11057369HCID 11057369, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent2×

Procedure

To n-butyllithium (7.28 mL of a 2.5 M solution in hexane, 18.2 mmol) at −5° C. was added dry THF (80 mL) dropwise, maintaining the temperature below 5° C. 5-Chloro-1-pentyne (7.75 mL , 73.1 mmol) was added at 5° C., and the solution was stirred for 3 hours. The reaction was quenched by the addition of tri-n-butyltin chloride (21.0 mL, 77.4 mmol), and was allowed to stir for an additional 10 min. The solution was poured into saturated aqueous NaHCO3 (500 mL) and hexane (500 mL). The hexane layer was washed with H2O (200 mL), then brine (200 mL), then dried over Na2SO4, filtered, and concentrated in vacuo to provide the titled product as a yellow oil.

Workup

  1. temperaturemaintaining the temperature below 5° C
  2. stirringto stir for an additional 10 min
  3. washThe hexane layer was washed with H2O (200 mL)
  4. dry with materialbrine (200 mL), then dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ba7d91eca79c40fcac7ce5bcf9894910
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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