Triethylene Glycol → 2-Undecylpyridine

HRID 1587708Notes

Reaction equation

HRID 1587708 reaction equation
[C:1]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].NN.[OH-].[K+].C(O)COCCOCCO>O>[CH2:1]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 8172Triethylene GlycolHCID 9321HydrazineHCID 14797Potassium HydroxideHCID 197561311-(Pyridin-2-yl)undecan-1-one

Product 1

HCID 5646402-UndecylpyridineYield 58.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 21.5 g (87 mmol) of 2-n-undecanoylpyridine, 13.7 g (0.27 mol) of hydrazine.monohydrate, 10.1 g (0.18 mol) of potassium hydroxide, and 50 ml of triethylene glycol was heated at 110° to 125° C. for one hour, and further, at 180° to 185° C. for 7 hours. After cooling, 400 ml of water was added, the mixture was extracted with diethyl ether, washed with water and dried over anhydrous potassium carbonate. After concentration under a reduced pressure, the residue was separated by silica gel column chromatography (ethyl acetate:hexane=1:9), and further, purified by distillation under a reduced pressure to give 11.9 g of the desired product (yield 58.7%).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with diethyl ether
  3. washwashed with water
  4. dry with materialdried over anhydrous potassium carbonate
  5. concentrationAfter concentration under a reduced pressure
  6. customthe residue was separated by silica gel column chromatography (ethyl acetate:hexane=1:9)
  7. distillationfurther, purified by distillation under a reduced pressure

Sources & evidence

ORD record
ord-e3121f8823d54f80b9eca4937d394a0f
Source dataset
uspto-grants-1993_06
Patent number
US05219847

Reaction notes

Loading…