Trimethyltin chloride → HCID 178442779, compound

HRID 2100218Notes

Reaction equation

HRID 2100218 reaction equation
[C:1]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].C([Li])CCC.C[Sn:22](Cl)(C)C.[Li]>O1CCCC1>[SnH3:22][SH:12]1[C:11]([C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:15][CH:14]=[CH:13]1

Participants

6

Reactant 4

HCID 14016Trimethyltin chloride2×HCID 3028194LithiumHCID 20870936HCID 20870936, compoundHCID 178418339Butyllithium

Product 1

HCID 178442779HCID 178442779, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a 1 L schlenk flask with egg-shaped stirbar in a glove box, the 2-decynylthiophene 22a (57.44 mmol, 12.658 g) was added by pipette. On a schlenk line, tetrahydrofuran (300 mL) was cannula transferred to the reaction vessel through a septum. The reaction mixture was cooled to −78° C. and n-butyl lithium (35.9 mL, 1.6 M solution in hexanes,) was added dropwise via syringe and the reaction mixture stirred for 45 min. The reaction vessel was fitted with an addition funnel and trimethyltin chloride (57.4 mL, 1.0 M solution in tetrahydrofuran) was cannula transferred to the funnel under positive argon pressure through a septum. The trimethyltin chloride solution was added dropwise to the stirring lithium salt solution over a period of 15 min. at −78° C. The reaction mixture was allowed to warm to ambient temperature with stirring overnight. The solvent was removed in vacuo on the schlenk line and trapped in a 1 L schienk flask. The resulting residue was dissolved in diethyl ether (500 mL) washed with brine (3×200 mL), dried over magnesium sulfate, filtered and the solvent removed by roto-evaporation to afford 1-stannyl-5-decynyl-thiophene 22b as a light brown oil (20.6 g, 94% yield). 1H NMR (CDCl3) δ 7.20 (d, 1H), 7.00 (d, 2H), 2.43 (t, 2H), 1.60 (m, 2H), 1.44(m, 2H), 1.30 (m, 8H), 0.899 (t, 3H), 0.37 (s, 9H); GC/MS (M+) 384 m/z, (M+-CH3) 369 m/z.

Workup

  1. customThe reaction vessel was fitted with an addition funnel
  2. temperatureto warm to ambient temperature
  3. stirringwith stirring overnight
  4. customThe solvent was removed in vacuo on the schlenk line
  5. customtrapped in a 1 L schienk flask
  6. dissolutionThe resulting residue was dissolved in diethyl ether (500 mL)
  7. washwashed with brine (3×200 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent removed by roto-evaporation

Sources & evidence

ORD record
ord-940f0e380e164052ada6940c42c48d32
Source dataset
uspto-grants-2009_08
Patent number
US07572393B2

Reaction notes

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