Ethylene Glycol → 1011487-86-7

HRID 242145Notes

Reaction equation

HRID 242145 reaction equation
CC(C)([O-])C.[K+].[CH2:7]([OH:10])[CH2:8][OH:9].Cl[C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][N:13]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[OH:9][CH2:8][CH2:7][O:10][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][N:13]=1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 516892Sodium BicarbonateHCID 27640536-Chloropyridine-3-carbaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 592786051011487-86-7

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.49 g (31.08 mmol) of potassium tert-butoxide are added to a solution of 3.51 g (56.51 mmol) of 1,2-ethanediol in 80 ml of dry DMF, and the mixture is stirred at RT for 15 min 4.0 g (28.26 mmol) of 6-chloronicotinaldehyde are then added. The reaction solution is stirred at RT for 20 h. The mixture is then poured into 200 ml of a 1:1 mixture of ethyl acetate and saturated sodium bicarbonate solution. The phases are separated, and the aqueous phase is then extracted with ethyl acetate (two times 100 ml each). The combined organic phases are washed with water (two times 100 ml each). The organic phase is dried over magnesium sulphate. After removal of the solvent on a rotary evaporator, the crude product is purified chromatographically on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 2:1).

Workup

  1. additionare then added
  2. customThe phases are separated
  3. extractionthe aqueous phase is then extracted with ethyl acetate (two times 100 ml each)
  4. washThe combined organic phases are washed with water (two times 100 ml each)
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. customAfter removal of the solvent
  7. customon a rotary evaporator
  8. customthe crude product is purified chromatographically on silica gel 60 (mobile phase: cyclohexane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-ed4db9337128468f978cba5d0e37e83c
Source dataset
uspto-grants-2014_02
Patent number
US08653109B2

Reaction notes

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