Bis(2-chloroethyl) ether → 4-(Pyridin-4-yl)oxane-4-carboxylic acid

HRID 1698352Notes

Reaction equation

HRID 1698352 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][C:8]([OH:10])=[O:9])=[CH:3][CH:2]=1.Cl[CH2:12][CH2:13][O:14][CH2:15][CH2:16]Cl>[OH-].[Na+].[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2([C:8]([OH:10])=[O:9])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 8115Bis(2-chloroethyl) etherHCID 342284-Pyridineacetic acid

Product 1

HCID 672728394-(Pyridin-4-yl)oxane-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

To a mixture of pyridin-4-yl-acetic acid (930 mg, 6.0 mmol) and bis-(2-chloroethyl)ether 1.1 mL, 9.0 mmol) in 50% NaOH aq. solution (5 mL) is added benzyltriethylammonium chloride (680 mg, 3 mmol). The solution is heated to 60° C. and stirred at the temperature for 2 hours. After cooling down to rt, the aqueous layer is removed and the organic layer is neutralized with sat. NH4Cl aq. and extracted with Et2O. The combined organic phases are washed with H2O and dried over Na2SO4. Concentration under reduced pressure gives the title compound. The material is used in a next step without purification.

Workup

  1. temperatureAfter cooling down to rt
  2. customthe aqueous layer is removed
  3. extractionextracted with Et2O
  4. washThe combined organic phases are washed with H2O
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-0006fce2f1564e3580e01d7c0bd0840e
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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