Ethyl Acetate → HCID 13603078, compound

HRID 704954Notes

Reaction equation

HRID 704954 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:15][C:16]([O:18][CH:19]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C(OCC)(=O)C>CN(C)C=O>[CH:19]([O:18][C:16]([CH2:15][N:5]1[CH:6]=[CH:7][C:2](=[O:1])[CH:3]=[CH:4]1)=[O:17])([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 20077950HCID 20077950, compoundHCID 178418642HCID 178418642, compound

Product 1

HCID 13603078HCID 13603078, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4 g (42.06 mmol) of 4-hydroxypyridine was dissolved in 80 ml of N,N-dimethylformamide, and 8.7 g (62.92 mmol) of potassium carbonate and 16.45 g (63 mmol) of benzhydryl α-chloroacetate were added thereto. After stirring for 4 hours at 60° C., 200 ml of ethyl acetate was added to the reaction solution, and washed, with water and a saturated sodium chloride aqueous solution followed by drying over anhydrous sodium sulfate and treating with active carbon. The solvent was distilled off under reduced pressure, and the crystal residue was washed with ether to obtain 9.8 g (yield: 73%) of 1-benzhydryloxycarbonylmethyl-4-pyridone.

Workup

  1. washwashed, with water
  2. dry with materialby drying over anhydrous sodium sulfate
  3. additiontreating with active carbon
  4. distillationThe solvent was distilled off under reduced pressure
  5. washthe crystal residue was washed with ether

Sources & evidence

ORD record
ord-279ce75a3dd448b0bcf3914f0590e58b
Source dataset
uspto-grants-1991_01
Patent number
US04988687

Reaction notes

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