Triethylamine → 5-(2-(Tert-butyldimethylsilyloxy)ethyl)thiophene-3-carbaldehyde

HRID 446385Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 446385
[Si:1]([O:8][CH2:9][CH2:10][C:11]1[S:15][C:14](Cl)=[C:13]([CH:17]=[O:18])[CH:12]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.[H][H]>[Pd].O.C(O)C.C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Si:1]([O:8][CH2:9][CH2:10][C:11]1[S:15][CH:14]=[C:13]([CH:17]=[O:18])[CH:12]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Komponenten

9

Edukt 3

HCID 8471TriethylamineHCID 579892115-(2-(Tert-butyldimethylsilyloxy)ethyl)-2-chlorothiophene-3-carbaldehydeHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 579889035-(2-(Tert-butyldimethylsilyloxy)ethyl)thiophene-3-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 23938PalladiumKatalysatorHCID 178418406HCID 178418406, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A slurry of palladium on carbon (10%, 0.28 g) in water (0.5 mL) was added cautiously to a solution of 5-(2-(tert-butyldimethylsilyloxy)ethyl)-2-chlorothiophene-3-carbaldehyde [Aromatic Intermediate 17, step 1)] (0.80 g) and triethylamine (0.91 mL) in ethanol (50 mL) and the resulting mixture stirred overnight under 4 bar pressure of hydrogen. The mixture was filtered through Celite and the filter pad washed with ethanol (10 mL). The combined filtrate and washings were evaporated and azeotroped with toluene (20 mL) to give a yellow oil. The residue was dissolved in DCM (100 mL), manganese dioxide (2.28 g) was added and the resulting suspension heated at reflux overnight. The mixture was filtered through Celite and the filter pad washed with DCM (50 mL). The combined filtrate and washings were evaporated to give the titled compound as a yellow oil. Yield 0.60 g.

Aufarbeitung

  1. filtrationThe mixture was filtered through Celite
  2. washthe filter pad washed with ethanol (10 mL)
  3. customThe combined filtrate and washings were evaporated
  4. customazeotroped with toluene (20 mL)
  5. customto give a yellow oil
  6. temperaturethe resulting suspension heated
  7. temperatureat reflux overnight
  8. filtrationThe mixture was filtered through Celite
  9. washthe filter pad washed with DCM (50 mL)
  10. customThe combined filtrate and washings were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-36b38f4e402d488293e78773bc276ecc
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476265B2

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