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

HRID 1285249Notes

Reaction equation

HRID 1285249 reaction equation
[C:1]([C:5]1[O:6][C:7]2[C:12]([C:13](=O)[CH:14]=1)=[CH:11][CH:10]=[C:9]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29](=O)[CH3:30])=[C:25]([OH:32])[C:24]=1[CH2:33][CH2:34][CH3:35])[C:8]=2[CH2:36][CH2:37][CH3:38])([O:3][CH3:4])=[O:2]>C(O)(=O)C.[Pd]>[C:1]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([CH2:36][CH2:37][CH3:38])[C:9]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][CH3:30])=[C:25]([OH:32])[C:24]=3[CH2:33][CH2:34][CH3:35])=[CH:10][CH:11]=2)[O:6]1)([O:3][CH3:4])=[O:2]

Participants

4

Reactant 1

HCID 135378622-Carbomethoxy-7-[5-(2-n-propyl-3-hydroxy-4-acetylphenoxy)pentoxy]-8-n-propylchromone

Product 1

HCID 202504642-Carbomethoxy-7-[5-(2-n-propyl-3-hydroxy-4-ethylphenoxy)pentoxy]-8-n-propylchromanYield 35%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

5.25 (10 mmole) of the compound from Example 5, was dissolved in 125 ml of glacial acetic acid and 0.5 g of 5% palladium on carbon added. The resulting suspension was hydrogenated at 70° C. and 50 psi for two hours. The reaction mixture was cooled and filtered to remove catalyst. After removing the solvent by rotary evaporation, the residue was purified by high pressure liquid chromatography to furnish 1.76 g (35%) of the title compound as an oil. Calc: C, 72.26; H, 8.49; Found: C, 72.20; H, 8.59.

Workup

  1. customwas hydrogenated at 70° C.
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered
  4. customto remove catalyst
  5. customAfter removing the solvent
  6. customby rotary evaporation
  7. customthe residue was purified by high pressure liquid chromatography

Sources & evidence

ORD record
ord-63a631b675444130b45df18249d6afc1
Source dataset
uspto-grants-1986_01
Patent number
US04565882

Reaction notes

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