Triethylamine → 1-(4-Methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-ethanone

HRID 390769Notes

Reaction equation

HRID 390769 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].Br[C:8]1[S:12][C:11]([C:13](=[O:15])[CH3:14])=[CH:10][C:9]=1[CH3:16].C(N(CC)CC)C>CN(C=O)C.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>[CH3:16][C:9]1[CH:10]=[C:11]([C:13](=[O:15])[CH3:14])[S:12][C:8]=1[C:6]#[C:5][Si:2]([CH3:4])([CH3:3])[CH3:1]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 454803531-(5-Bromo-4-methylthiophen-2-yl)ethan-1-one

Product 1

HCID 674301401-(4-Methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-ethanone

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Trimethylsilylacetylene (16 ml) is added to a solution of 1-(5-bromo-4-methyl-thiophen-2-yl)-ethanone (16.9 q, example 1, step A), Pd(PPh3)2Cl2 (3.78 g), CuI (1.46 g) and triethylamine (16 ml) in DMF (15 ml). After 3 hours at room temperature, the reaction is quenched with water and extracted three times with ethyl acetate. The organic phases are combined, dried over Na2SO4 and concentrated in vacuo. The crude product is purified by filtration over a plug of silica gel eluting with dichloromethane to yield 1-(4-methyl-5-trimethylsilanylethynyl-thiophen-2-yl)-ethanone (18.2 g) as yellow solid. The compound is used without further purification.

Workup

  1. customthe reaction is quenched with water
  2. extractionextracted three times with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. filtrationThe crude product is purified by filtration over a plug of silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-47a109eae293408b818b08e6b8721a45
Source dataset
uspto-grants-2013_02
Patent number
US08383659B2

Reaction notes

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