2-Carboethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)pentoxy]-8-n-propylchromone → 2-Carboethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)pentoxy]-8-n-propylchroman-4-one

HRID 1285244Notes

Reaction equation

HRID 1285244 reaction equation
[C:1]([C:6]1[O:7][C:8]2[C:13]([C:14](=[O:16])[CH:15]=1)=[CH:12][CH:11]=[C:10]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30](=[O:32])[CH3:31])=[C:26]([OH:33])[C:25]=1[CH2:34][CH2:35][CH3:36])[C:9]=2[CH2:37][CH2:38][CH3:39])([O:3][CH2:4][CH3:5])=[O:2]>C(O)C.[Ni]>[C:1]([CH:6]1[CH2:15][C:14](=[O:16])[C:13]2[C:8](=[C:9]([CH2:37][CH2:38][CH3:39])[C:10]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([C:30](=[O:32])[CH3:31])=[C:26]([OH:33])[C:25]=3[CH2:34][CH2:35][CH3:36])=[CH:11][CH:12]=2)[O:7]1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 1

HCID 135378612-Carboethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)pentoxy]-8-n-propylchromone

Product 1

HCID 202504682-Carboethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)pentoxy]-8-n-propylchroman-4-oneYield 51.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

2.45 g (4.55 mmole) of the compound from Example 2 was dissolved in 250 ml of absolute ethanol, 0.5 g W2Raney nickel added, and the mixture hydrogenated at 2 psi and room temperature for 7 hours. After removal of catalyst by filtration and solvent by rotary evaporation, the residue was purified by high pressure liquid chromatography to furnish 1.26 g (51%) of the title compound, mp 80°-81°. Calc: C, 68.87; H, 7.46. Found: C, 68.70; H. 7.43.

Workup

  1. customAfter removal of catalyst
  2. filtrationby filtration and solvent
  3. customby rotary evaporation
  4. customthe residue was purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-721ba1af985546429bac2c1460da872c
Source dataset
uspto-grants-1986_01
Patent number
US04565882

Reaction notes

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