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

HRID 1689533ノート

反応式

HRID 1689533 の反応式
[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]

参加物

8

反応物 2

HCID 579892115-(2-(Tert-butyldimethylsilyloxy)ethyl)-2-chlorothiophene-3-carbaldehydeHCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 5

HCID 23938Palladium触媒HCID 178418406HCID 178418406、化合物触媒HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7ae672166d9043919c3f521234eb4e96
出典データセット
uspto-grants-2012_04
特許番号
US08148373B2

反応ノート

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