Sodium Acetate → HCID 15919157, compound

HRID 1081524Notes

Reaction equation

HRID 1081524 reaction equation
C([O-])(=O)C.[Na+].[CH2:6]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:26]=[C:25](Cl)[C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:23][N:22]=2)=[CH:17][CH:16]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[H][H]>O1CCOCC1.[Pd]>[CH2:6]([O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[N:22]=[CH:23][C:24]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:25][N:26]=2)=[CH:17][CH:16]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 23362616HCID 23362616, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 15919157HCID 15919157, compoundYield 111.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Six (6) g of hydrogenation catalyst in which 5 % of Pd was carried on activated carbon and a small amount of sodium acetate were placed in an eggplant-shaped flask. After replacing the atmosphere inside the flask with nitrogen, 6 g of the above Compound D dissolved in 90 ml of dioxane was slowly dropped into the flask through a dropping funnel. After replacing the inside atmosphere with hydrogen with stirring, hydrogen was supplied from a gas reservoir. The reaction was continued until hydrogen absorption ceased. Thereafter the atmosphere was replaced with nitrogen, and the catalyst was removed by filtration. The solvent was recovered from the filtrate. Thus obtained crude product was purified by column chromatography and recrystallization to provide 6.1 g of purified 2-(4-octyloxyphenyl)-5- ethoxycarbonylpyrimidine (Compound E).

Workup

  1. additionwas slowly dropped into the flask through a dropping funnel
  2. customThe reaction was continued until hydrogen absorption
  3. customthe catalyst was removed by filtration
  4. customThe solvent was recovered from the filtrate
  5. customThus obtained crude product
  6. customwas purified by column chromatography and recrystallization

Sources & evidence

ORD record
ord-e69a65ee5681407a87c3a61141e4b526
Source dataset
uspto-grants-1996_12
Patent number
US05587106

Reaction notes

Loading…