2-Chloroethanol → HCID 11673597, compound

HRID 1958213Notes

Reaction equation

HRID 1958213 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 hours. The reaction mixture was cooled to room temperature 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 hours
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-ffef3a2e02e84d24988728148bee4d6f
Source dataset
uspto-grants-2013_04
Patent number
US08410109B2

Reaction notes

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