Tributyltin Chloride → HCID 11057369, compound

HRID 2251964Notes

Reaction equation

HRID 2251964 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]>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

5

Reactant 3

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

Product 1

HCID 11057369HCID 11057369, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of n-butyllithium (2.5M in hexanes, 159 mL, 0.398 mol) in THF (800 mL) at −10° C. under nitrogen, add 5-chloropentyne (20 g, 0.195 mol) dropwise, keeping the temperature below 10° C. After the addition is complete, allow the reaction to warm to room temperature and stir for 6 hours, then add tributyltin chloride (70 g, 0.215 mol) and stir overnight. Pour the reaction mixture into hexanes (500 mL), wash with saturated sodium bicarbonate (300 mL) and brine (300 mL), dry with sodium sulfate, filter, and concentrate to afford the title compound (70 g, 100%) which can be used without further purification: mass spectrum (m/e): 357 (M+H+); 1H NMR (CDCl3) δ 1.70-1.49 (m, 6H), 1.49-1.24 (m, 7H), 1.10-0.65 (m, 19H).

Workup

  1. customthe temperature below 10° C
  2. additionAfter the addition
  3. customthe reaction
  4. washwash with saturated sodium bicarbonate (300 mL) and brine (300 mL)
  5. dry with materialdry with sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-dd442acf22044bb7b1ba55ac42d98779
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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