Dimethylformamide → 3-[4-(Ethoxycarbonylmethyloxymethyl)phenylcarbonyl]pyridine

HRID 2303937Notes

Reaction equation

HRID 2303937 reaction equation
[H-].[Na+].CN(C=O)C.[OH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[O:17])=[CH:12][CH:11]=1.[C:24]([O:27][CH2:28][CH2:29]Br)(=[O:26])[CH3:25]>O>[CH2:28]([O:27][C:24]([CH2:25][O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)=[O:17])=[CH:14][CH:15]=1)=[O:26])[CH3:29]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 135641-Acetoxy-2-bromoethaneHCID 24758Sodium hydrideHCID 184620204-(Pyridine-3-carbonyl)-benzyl alcohol

Product 1

HCID 184620193-[4-(Ethoxycarbonylmethyloxymethyl)phenylcarbonyl]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

150 mg of 60% sodium hydride was gradually added to 10 ml of a DMF solution of 666 mg of 3-[4-(hydroxymethyl)phenylcarbonyl]pyridine under ice cooling. The reaction solution was stirred at room temperature for 1 hour, then 0.4 ml of 2-bromoethyl acetate was added and the mixture was stirred under the same reaction conditions for 3 hours. After the reaction was completed, the reactive product was diluted with water, extracted with ethyl acetate, and the resultant product was washed with brine, then dried over magnesium sulfate, filtered, and concentrated in vacuo to obtain the desired compound in an amount of 336 mg.

Workup

  1. stirringthe mixture was stirred under the same reaction conditions for 3 hours
  2. extractionextracted with ethyl acetate
  3. washthe resultant product was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-30880ee29725423b82c3fe42d8439aaa
Source dataset
uspto-grants-2002_08
Patent number
US06433167B1

Reaction notes

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