Triethylamine → Methyl 1-(3-methylbutenyl)-1,4,5,6-tetrahydro-3-pyridyl ketone

HRID 359315ノート

反応式

HRID 359315 の反応式
[Br-].[CH3:2][C:3]([CH3:15])=[CH:4][CH2:5][N+:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12](=[O:14])[CH3:13])[CH:7]=1.C(N(CC)CC)C.[H][H]>C(O)C.[Pd]>[CH3:2][CH:3]([CH3:15])[CH:4]=[CH:5][N:6]1[CH2:11][CH2:10][CH2:9][C:8]([C:12]([CH3:13])=[O:14])=[CH:7]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 189633631-(3-Methyl-2-butenyl)-3-acetyl-pyridinium bromideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 53639438Methyl 1-(3-methylbutenyl)-1,4,5,6-tetrahydro-3-pyridyl ketone

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

1-(3-methyl-2-butenyl)-3-acetyl-pyridinium bromide (27.0 g, 0.1 mole) and triethylamine (10.1 g, 0.1 mole) in ethyl alcohol (50 ml) over 5% palladium on carbon (5 g) was hydrogenated at room temperature and pressure until two molar equivalents of hydrogen was taken up. The catalyst was removed by filtration and the filtrate concentrated at reduced pressure. The semi-solid residue was diluted with diethyl ether (75 ml), the solid removed by filtration and the filtrate concentrated under reduced pressure to leave a pale oil which solidified on standing. Recrystallisation from ethanol/water gave the product, methyl 1-(3-methylbutenyl)-1,4,5,6-tetrahydro-3-pyridyl ketone (4) as a pale yellow crystalline solid m.p 76-78°C.

後処理

  1. customwas hydrogenated at room temperature
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate concentrated at reduced pressure
  4. additionThe semi-solid residue was diluted with diethyl ether (75 ml)
  5. customthe solid removed by filtration
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customto leave a pale oil which
  8. customRecrystallisation from ethanol/water

出典と根拠

ORDレコード
ord-1d75396f0e574652aa12d434a6591622
出典データセット
uspto-grants-1991_03
特許番号
US05000946

反応ノート

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