Triethylamine → Methyl 1-(3-methylbutenyl)-1,4,5,6-tetrahydro-3-pyridyl ketone
Reaction equation
[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]1Participants
6
Procedure
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.
Workup
- customwas hydrogenated at room temperature
- customThe catalyst was removed by filtration
- concentrationthe filtrate concentrated at reduced pressure
- additionThe semi-solid residue was diluted with diethyl ether (75 ml)
- customthe solid removed by filtration
- concentrationthe filtrate concentrated under reduced pressure
- customto leave a pale oil which
- customRecrystallisation from ethanol/water
Sources & evidence
- ORD record
- ord-1d75396f0e574652aa12d434a6591622
- Source dataset
- uspto-grants-1991_03
- Patent number
- US05000946
Reaction notes
Loading…