2-Chloroethanol → HCID 11673597, compound

HRID 418847Notes

Reaction equation

HRID 418847 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-ce09ccea95174e75aa5259dcdb011852
Source dataset
uspto-grants-2012_01
Patent number
US08093273B2

Reaction notes

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