Triethylamine → 4-((Trimethylsilyl)ethynyl)thiophene-2-carbaldehyde

HRID 2247674Notes

Reaction equation

HRID 2247674 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[S:5][CH:6]=1.[CH3:9][Si:10]([C:13]#[CH:14])([CH3:12])[CH3:11].C(N(CC)CC)C.[Cl-].[NH4+]>CN(C)C=O.C(OCC)(=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>[CH3:9][Si:10]([C:13]#[C:14][C:2]1[CH:3]=[C:4]([CH:7]=[O:8])[S:5][CH:6]=1)([CH3:12])[CH3:11]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 66111TrimethylsilylacetyleneHCID 877924-Bromothiophene-2-carbaldehyde

Product 1

HCID 513459824-((Trimethylsilyl)ethynyl)thiophene-2-carbaldehydeYield 100%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-bromo-2-thiophenecarboxaldehyde (3.0 g, 16 mmol) in N,N-dimethylformamide (30 ml) were added successively (trimethylsilyl)acetylene (11 ml, 79 mmol), triethylamine (13 ml, 94 mmol), and dichlorobis(triphenylphosphine)palladium (1.1 g, 1.6 mmol) under a nitrogen atmosphere with stirring, and the resulting mixture was stirred at 80° C. for 2 hours under a nitrogen atmosphere. After stirring, the reaction mixture was diluted with ethyl acetate, poured into a saturated aqueous solution of ammonium chloride (250 ml) and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. After filtration, the filtrate was evaporated in vacuo, and the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (0:1 to 1:19) as the eluent to afford the title compound (3.3 g) in a yield of 100% as a brown oily product.

Workup

  1. stirringthe resulting mixture was stirred at 80° C. for 2 hours under a nitrogen atmosphere
  2. stirringAfter stirring
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationAfter filtration
  7. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-6e7f04e9baa44af4a20278109afca292
Source dataset
uspto-grants-2010_03
Patent number
US07687491B2

Reaction notes

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