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Ethyl Acetate → HCID 13603078, compound

HRID 1638847
Notes
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Reaction equation

HRID 1638847 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].Cl[CH2:13][C:14]([O:16][CH:17]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].C(OCC)(=O)C>CN(C)C=O>[CH:17]([O:16][C:14]([CH2:13][N:5]1[CH:6]=[CH:7][C:2](=[O:1])[CH:3]=[CH:4]1)=[O:15])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 19660Carbonate IonHCID 20077950HCID 20077950, compoundHCID 178418642HCID 178418642, compound

Product 1

HCID 13603078HCID 13603078, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

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 pottasium 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-4e22c8a6b412484594cf3642816b1db2
Source dataset
uspto-grants-1989_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04880797

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes