Chloride → HCID 23045067, compound

HRID 2108038Notes

Reaction equation

HRID 2108038 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.O.O.O.C([O-])(=[O:22])C.[Na+].[Cl-].[OH-].[Na+]>C(O)C.O>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[CH2:10][CH2:9][O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][OH:22]

Participants

7

Reactant 4

HCID 312ChlorideHCID 14798Sodium HydroxideHCID 151669352-(2-((6-Bromohexyl)oxy)ethyl)pyridineHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 23045067HCID 23045067, compoundYield 70.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2-[2[(6-bromohexyl)oxy]ethyl]pyridine (9.0 g), sodium acetate trihydrate (34.24 g), trictylpropylammonium chloride (1.9 g) and water (25 ml) was stirred under reflux for 2 h. 2N sodium hydroxide solution (50 ml) and ethanol (50 ml) were added to the cooled mixture which was further stirred for 10 min at room temperature. The ethanol was evaporated in vacuo and the residue diluted with brine (150 ml) and extracted with ether (2×100 ml). The combined organic extracts were washed successively with water (150 ml), brine (100 ml), dried and evaporated in vacuo to give a yellow oil. Purification by FCC eluting with ether gave the title compound as a colourless oil (4.94 g), t.l.c. (ether) Rf 0.31.

Workup

  1. temperatureunder reflux for 2 h
  2. stirringwas further stirred for 10 min at room temperature
  3. customThe ethanol was evaporated in vacuo
  4. additionthe residue diluted with brine (150 ml)
  5. extractionextracted with ether (2×100 ml)
  6. washThe combined organic extracts were washed successively with water (150 ml), brine (100 ml)
  7. customdried
  8. customevaporated in vacuo
  9. customto give a yellow oil
  10. customPurification by FCC
  11. washeluting with ether

Sources & evidence

ORD record
ord-b33a78045b404174a55607e197708d3d
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

Loading…