Acetyl chloride → (5-(Benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl acetate

HRID 1510689Notes

Reaction equation

HRID 1510689 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:17])[CH:11]=[C:12]([CH2:15][OH:16])[NH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](Cl)(=[O:20])[CH3:19]>N1C=CC=CC=1>[C:18]([O:16][CH2:15][C:12]1[NH:13][CH:14]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:10](=[O:17])[CH:11]=1)(=[O:20])[CH3:19]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 28015645-(Benzyloxy)-2-(hydroxymethyl)-1,4-dihydropyridin-4-one

Product 1

HCID 57815284(5-(Benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 10 g of 5-(benzyloxy)-2-(hydroxymethyl)pyridin-4(1H)-one in 58 mL of pyridine, 4.6 mL of acetyl chloride was added under cooling with ice, and the mixture was stirred at 60 to 70° C. for 3 hours. The solvent was distilled off under reduced pressure, water was added thereto, and the mixture was stirred under cooling with ice. The solid was filtered off, chloroform was added thereto and the resultant was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. Thereto was added diethyl ether and the solid was filtered off to obtain 9.2 g of (5-(benzyloxy)-4-oxo-1,4-dihydropyridin-2-yl)methyl acetate as a light brown solid.

Workup

  1. temperatureunder cooling with ice
  2. distillationThe solvent was distilled off under reduced pressure, water
  3. additionwas added
  4. stirringthe mixture was stirred
  5. temperatureunder cooling with ice
  6. filtrationThe solid was filtered off
  7. additionchloroform was added
  8. dry with materialthe resultant was dried over anhydrous magnesium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. additionThereto was added diethyl ether
  11. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-012af917765543a2b721dd328b63f2ea
Source dataset
uspto-grants-2012_07
Patent number
US08211908B2

Reaction notes

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