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

HRID 1707337노트

반응식

HRID 1707337 반응식
[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

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 189633631-(3-Methyl-2-butenyl)-3-acetyl-pyridinium bromideHCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d19478e9f658482895205f1d7c658952
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05352793

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