Phosphate → 6-[2-(Pyridin-2-yl)ethoxy]hexanoic acid

HRID 2108040Notes

Reaction equation

HRID 2108040 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:18].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.P([O-])([O-])([O-])=O.[Na+].[Cl-]>CN(C=O)C.O.ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:18])=[O:16]

Participants

8

Reactant 4

HCID 1061PhosphateHCID 5234Sodium ChlorideHCID 2724130Cornforth reagentHCID 23045067HCID 23045067, compound

Product 1

HCID 151669416-[2-(Pyridin-2-yl)ethoxy]hexanoic acidYield 51.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 6-[2-(2-pyridinyl)ethoxy]hexanol (1.0 g) and pyridinium dichromate (5.90 g) in DMF (12 ml) was stirred at room temperature for 24 h. The solution was diluted with water (100 ml) and extracted with ether (2×100 ml). The combined organic extracts were washed with water (100 ml), dried and evaporated in vacuo to give a colourless oil. The original aqueous washes were combined and re-extracted with dichloromethane (2×150 ml), washed with water (100 ml), dried and evaporated in vacuo to give a brown oil. The original aqueous washes were then buffered to pH 6.5 using phosphate buffer and solid NaCl added. The saturated solution was extracted with dichloromethane (2×100 ml), washed with water (100 ml), dried and evaporated in vacuo to give a brown oil. The three oils were combined and purified by FCC eluting with hexane-ether (1:1) followed by methanol to afford a yellow oil, which was dissolved in dichloromethane (50 ml) and filtered. The filtrate was evaporated in vacuo to give the title compound as a green oil (0.55 g), t.l.c. (System A 40:10:1) Rf 0.6.

Workup

  1. extractionextracted with ether (2×100 ml)
  2. washThe combined organic extracts were washed with water (100 ml)
  3. customdried
  4. customevaporated in vacuo
  5. customto give a colourless oil
  6. extractionre-extracted with dichloromethane (2×150 ml)
  7. washwashed with water (100 ml)
  8. customdried
  9. customevaporated in vacuo
  10. customto give a brown oil
  11. additionadded
  12. extractionThe saturated solution was extracted with dichloromethane (2×100 ml)
  13. washwashed with water (100 ml)
  14. customdried
  15. customevaporated in vacuo
  16. customto give a brown oil
  17. custompurified by FCC
  18. washeluting with hexane-ether (1:1)
  19. customto afford a yellow oil, which
  20. filtrationfiltered
  21. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-ef0187a8165a4f2c9e81bf6c3ae22c15
Source dataset
uspto-grants-1990_06
Patent number
US04937251

Reaction notes

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