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

HRID 471305Notes

Reaction equation

HRID 471305 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].[H][H]>C(O)C.C(N(CC)CC)C.[Pd].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

8

Reactant 2

HCID 579892115-(2-(Tert-butyldimethylsilyloxy)ethyl)-2-chlorothiophene-3-carbaldehydeHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 178418406HCID 178418406, compoundCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

5-(2-(tert-butyldimethylsilyloxy)ethyl)-2-chlorothiophene-3-carbaldehyde (0.8 g) (example 278, step b) in a mixture of ethanol (50 mL) and triethylamine (0.91 mL) with 10% palladium on carbon catalyst (0.28 g) was stirred vigorously under 4 bar pressure of hydrogen for 18 hours. The mixture was filtered through celite and the filter pad washed with ethanol (50 mL). The combined filtrate and washings were evaporated and azeotroped with toluene (20 mL) to give a yellow oil. The oil was dissolved in DCM (100 mL), manganese dioxide (2.3 g) was added and the resulting suspension refluxed overnight. The mixture was filtered through celite and the filter pad washed with DCM (50 mL). The combined filtrate and washings were evaporated in vacuo to give the subtitled compound as a yellow oil. Yield 0.6 g.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washthe filter pad washed with ethanol (50 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 refluxed overnight
  7. filtrationThe mixture was filtered through celite
  8. washthe filter pad washed with DCM (50 mL)
  9. customThe combined filtrate and washings were evaporated in vacuo

Sources & evidence

ORD record
ord-c295184d2f58406f96d97655accd3afd
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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