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

HRID 1255261노트

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HRID 1255261 반응식
[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]

참가 물질

9

반응물 3

HCID 8471TriethylamineHCID 579892115-(2-(Tert-butyldimethylsilyloxy)ethyl)-2-chlorothiophene-3-carbaldehyde2회HCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 5

HCID 23938Palladium촉매HCID 178418406HCID 178418406, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-878ffb4abf7e45cc82021f2c0d83c49b
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455483B2

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