2-Chloroethanol → HCID 11673597, compound

HRID 884701Notes

Reaction equation

HRID 884701 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:17][C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[C:10](=[O:18])[CH:9]=2)=[CH:4][CH:3]=1.Cl[CH2:20][CH2:21][OH:22]>CCO.C(#N)C>[OH:22][CH2:21][CH2:20][O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:17][C:12]3=[N:13][CH:14]=[CH:15][CH:16]=[C:11]3[C:10](=[O:18])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 342-ChloroethanolHCID 116300742-(4-Hydroxyphenyl)-4H-pyrano[2,3-b]pyridin-4-one

Product 1

HCID 11673597HCID 11673597, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6342AcetonitrileSolvent

Procedure

In a 100 mL dry round bottom flask with reflux condenser and magnetic stirrer was placed 2-(4-hydroxy-phenyl)-pyrano[2,3-b]pyridin-4-one (1.0 g, 4.18 mmol) in EtOH (10 mL) and acetonitrile (50 mL). 2-Chloroethanol (2.05 g, 25.0 mmol) was added slowly and the reaction mixture was refluxed for 48 h. The reaction mixture was cooled to rt and concentrated under reduced pressure. The crude product was purified by column chromatography, using 2% MeOH in dichloromethane to afford 2-(4-(2-hydroxyethoxy)phenyl)-4H-pyrano[2,3-b]pyridine-4-one (380 mg, 32% yield). MS (ES) m/z: 284.94 (M+1), 283.95 (M); Mp. 157-159° C.

Workup

  1. customIn a 100 mL dry round bottom flask
  2. temperaturewith reflux condenser and magnetic stirrer
  3. temperaturethe reaction mixture was refluxed for 48 h
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-156ae2d87b9a48099cdef2d1fa76a9cd
Source dataset
uspto-grants-2012_08
Patent number
US08242130B2

Reaction notes

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