Ethylene Glycol → HCID 59665583, compound

HRID 1254094Notes

Reaction equation

HRID 1254094 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[N:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=2)[CH2:4][O:3]1.[CH2:13](O)[CH2:14][OH:15].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C1C=CC=CC=1>[O:12]1[CH2:13][CH2:14][O:15][CH:11]1[C:7]1[N:6]=[C:5]2[CH2:4][O:3][C:2](=[O:1])[C:10]2=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 58478784HCID 58478784, compound

Product 1

HCID 59665583HCID 59665583, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 5-oxo-5,7-dihydro-furo[3,4-b]pyridine-2-carbaldehyde (100 mg, 0.61 mmol) in anhydrous benzene (5 mL) is added ethylene glycol (0.1 mL, 1.77 mmol), a catalytic amount p-toluenesulfonic acid monohydrate and 4 Å mole sieves. The reaction mixture is heated at a reflux temperature for 20 h. The reaction mixture is allowed to cool to room temperature and saturated. aqueous NaHCO3 solution is added. The resulting mixture is filtered through celite, washed with saturated aqueous NaHCO3 and EtOAc. The isolated organic layer is washed with brine (1×), dried with anhydrous Na2SO4, and concentrated. The residue is treated with EtOAc-Hexane (1:4) and the light brown solid which forms is collected by filtration and dried to give the title compound (42 mg, 33%).

Workup

  1. temperatureThe reaction mixture is heated at a reflux temperature for 20 h
  2. filtrationThe resulting mixture is filtered through celite
  3. washwashed with saturated aqueous NaHCO3 and EtOAc
  4. washThe isolated organic layer is washed with brine (1×)
  5. dry with materialdried with anhydrous Na2SO4
  6. concentrationconcentrated
  7. additionThe residue is treated with EtOAc-Hexane (1:4)
  8. filtrationthe light brown solid which forms is collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-61aa5c864ce44ea28b870730691b23cc
Source dataset
uspto-grants-2013_06
Patent number
US08455535B2

Reaction notes

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