Tetrahydrofuran → HCID 18963375, compound

HRID 359316Notes

Reaction equation

HRID 359316 reaction equation
[C:1]([C:4]1[CH2:9][CH2:8][CH2:7][NH:6][CH:5]=1)(=[O:3])[CH3:2].[H-].[Na+].O1CCCC1.Br[CH2:18][CH:19]([CH2:24][CH3:25])[CH2:20][CH2:21][CH2:22][CH3:23]>O>[CH2:24]([CH:19]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:18][N:6]1[CH2:7][CH2:8][CH2:9][C:4]([C:1]([CH3:2])=[O:3])=[CH:5]1)[CH3:25]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 868042-Ethylhexyl bromideHCID 32845951-(1,4,5,6-tetrahydropyridin-3-yl)ethanone

Product 1

HCID 18963375HCID 18963375, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-acetyl-1,4,5,6-tetrahydropyridine (20.0 g, 0.16 mole) was added under nitrogen to a mixture of sodium hydride (5.76 g, 0.24 mole) and dry tetrahydrofuran (50 ml) stirring at room temperature. After one hour, 1-bromo-2-ethyl hexane (33.8 g, 0.175 mole) was added dropwise over 15 minutes and the mixture stirred overnight at room temperature. The reaction mixture was cautiously added to iced water (100 g) under nitrogen and extracted with diethyl ether (3×100 ml). The combined organic phase was dried over magnesium sulphate, concentrated under reduced pressure and the residue distilled to give methyl 1-(2-ethylhexyl)-1,4,5,6-tetrahydro-3-pyridyl ketone (5) as a pale yellow oil (b.pt 140-142°C./0.1 mm Hg).

Workup

  1. stirringthe mixture stirred overnight at room temperature
  2. extractionextracted with diethyl ether (3×100 ml)
  3. dry with materialThe combined organic phase was dried over magnesium sulphate
  4. concentrationconcentrated under reduced pressure
  5. distillationthe residue distilled

Sources & evidence

ORD record
ord-987f7eecff964146807e115e58df15c4
Source dataset
uspto-grants-1991_03
Patent number
US05000946

Reaction notes

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