Water → 2-[(Trimethylsilyl)ethynyl]thiophene

HRID 705004Notes

Reaction equation

HRID 705004 reaction equation
I[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.C(NC(C)C)(C)C.[CH3:14][Si:15]([C:18]#[CH:19])([CH3:17])[CH3:16].O>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:14][Si:15]([CH3:17])([CH3:16])[C:18]#[C:19][C:2]1[S:3][CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 962WaterHCID 7912DiisopropylamineHCID 189212-IodothiopheneHCID 66111Trimethylsilylacetylene

Product 1

HCID 5968702-[(Trimethylsilyl)ethynyl]thiopheneYield 69,747.898%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-iodothiophene (500 mg, 2.38 mmol), Pd(PPh3)2Cl2 (52.95 mg, 0.0754 mmol), CuI (28.1 mg, 0.14756 mmol) and diisopropylamine (0.62 ml, 4.4744 mmol) in THF (4 ml) was degassed thoroughly with argon, and trimethylsilyl acetylene (0.453 ml, 3.284 mmol) was added at room temperature. After stirring the reaction mixture for 16 hours at room temperature, it was poured into water and extracted with dichloromethane. The combined organic layers were washed with brine and dried over anhydrous sodium sulfate, and the solvent was evaporated. The crude material was purified by column chromatography (100-200 mesh silica gel) using hexane as eluent to yield 300 mg of trimethyl(thiophen-2-ylethynyl)silane (300 mg, 1.66 mol, yield 70.02%).

Workup

  1. additionwas added at room temperature
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThe crude material was purified by column chromatography (100-200 mesh silica gel)

Sources & evidence

ORD record
ord-6233443a8a7c4402869d8e98a8013d67
Source dataset
uspto-grants-2015_11
Patent number
US09173401B2

Reaction notes

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