Cesium carbonate → 4-Pyridyloxyundecan-1-ol

HRID 278286

Reaction equation

HRID 278286 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26]>CN(C=O)C>[N:5]1[CH:6]=[CH:7][C:2]([O:1][CH:25]([OH:26])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 7416311-Bromo-1-undecanolHCID 178418642HCID 178418642, compound

Product 1

HCID 226277984-Pyridyloxyundecan-1-olYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

The compound 4-pyridyloxyundecan-1-ol was prepared as follows: To a solution of 4-hydroxy-pyridine (5.71 g, 60 mmol) in DMF (150 cm3) was added cesium carbonate (19.56 g, 60 mmol). The mixture was heated to 90° C. for 5 mins then 11-bromoundecanol (12.56 g, 50 mmol) was added and the mixture heated to reflux temperature (125° C.) for 15 hours. After cooling, the contents of the flask were poured into rapidly stirring distilled water (800 cm3). A pale yellow precipitate formed which was filtered and dried (in air). Recrystallization from hexane gave white crystals of 4-pyridyloxyundecan-1-ol (2.9 g, 22%).

Workup

  1. customThe compound 4-pyridyloxyundecan-1-ol was prepared
  2. temperaturethe mixture heated
  3. temperatureto reflux temperature (125° C.) for 15 hours
  4. temperatureAfter cooling
  5. additionthe contents of the flask were poured
  6. distillationdistilled water (800 cm3)
  7. customA pale yellow precipitate formed which
  8. filtrationwas filtered
  9. customdried (in air)
  10. customRecrystallization from hexane

Sources & evidence

ORD record
ord-b20d2e813885471983fcc0bca3358792
Source dataset
uspto-grants-2002_03
Patent number
US06359056B1

Linked notes

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