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

HRID 1255261Notes

Reaction equation

HRID 1255261 reaction equation
[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]

Participants

9

Reactant 3

HCID 8471TriethylamineHCID 579892115-(2-(Tert-butyldimethylsilyloxy)ethyl)-2-chlorothiophene-3-carbaldehyde2×HCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 178418406HCID 178418406, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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 b] (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.

Workup

  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

Sources & evidence

ORD record
ord-878ffb4abf7e45cc82021f2c0d83c49b
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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