Tributyltin Chloride → HCID 69155245, compound

HRID 2251963Notes

Reaction equation

HRID 2251963 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[CH:2].C([Li])CCC.[CH2:14]([Sn:18](Cl)([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:16][CH3:17]>C1COCC1.CCOCC>[CH2:23]([Sn:18]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:19][CH2:20][CH2:21][CH3:22])[C:2]#[C:1][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[CH2:24][CH2:25][CH3:26]

Participants

6

Reactant 3

HCID 15096Tributyltin ChlorideHCID 137268EthynylpyridineHCID 178418339Butyllithium

Product 1

HCID 69155245HCID 69155245, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 2-ethynylpyridine (7.14 g, 69.23 mmol) in THF (350 mL) and cool the solution to −10° C. (ice/methanol) under nitrogen. Add n-butyllithium (1.6 M in hexanes, 47.6 mL, 76.16 mmol) dropwise and stir the mixture. After 15 minutes, add tributyltin chloride (20.7 mL, 76.2 mL) dropwise. Warn the mixture to room temperature overnight. Quench the reaction with water, dilute with ether, and wash with saturated ammonium chloride, then brine. Dry over sodium sulfate, filter and concentrate. No further purification necessary to give the title compound: 1H NMR (CDCl3) δ 8.50-8.54 (m, 1H), 7.51-7.59 (m, 1H), 7.35-7.43 (m, 1H), 7.11-7.18 (m, 1H), 1.59-1.64 (m, 6H), 1.32-1.42 (m, 6H), 1.05-1.10 (m, 6H), 0.88-0.94 (m, 9H).

Workup

  1. customto room temperature
  2. customovernight
  3. customQuench
  4. customthe reaction with water
  5. washwash with saturated ammonium chloride
  6. dry with materialDry over sodium sulfate
  7. filtrationfilter
  8. concentrationconcentrate
  9. customNo further purification necessary

Sources & evidence

ORD record
ord-eec3f70065934764b84f3f0081e7baae
Source dataset
uspto-grants-2008_01
Patent number
US07320994B2

Reaction notes

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