1,6-Dibromohexane → 3-[2-[(6-Bromohexyl)oxy]ethoxy]pyridine

HRID 2108128Notes

Reaction equation

HRID 2108128 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([O:7][CH2:8][CH2:9][OH:10])[CH:2]=1.[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.[OH-].[Na+]>S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:10][CH2:9][CH2:8][O:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 123681,6-DibromohexaneHCID 14798Sodium HydroxideHCID 219089972-(Pyridin-3-yloxy)ethan-1-ol

Product 1

HCID 230452653-[2-[(6-Bromohexyl)oxy]ethoxy]pyridine

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

A mixture of 2-[(3-pyridinyl)oxy]ethanol (1.9 g), 1,6-dibromohexane (6 ml), tetra-n-butylammonium bisulphate (0.5 g) and 50% w/v sodium hydroxide (20 ml) was stirred vigorously for 5 h, diluted with water (30 ml) and extracted with ethyl acetate (3×50 ml). The combined organic extracts were dried and evaporated in vacuo to give an oil which was purified by FCC eluting with hexane→ethylacetate to give the title compound (2.3 g) as an oil. T.l.c. (System E 80:20:1) Rf 0.63

Workup

  1. extractionextracted with ethyl acetate (3×50 ml)
  2. customThe combined organic extracts were dried
  3. customevaporated in vacuo
  4. customto give an oil which
  5. customwas purified by FCC
  6. washeluting with hexane→ethylacetate

Sources & evidence

ORD record
ord-388867c26e6b4f08b8296cf56559f8f1
Source dataset
uspto-grants-1990_06
Patent number
US04937268

Reaction notes

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