2-Carboethoxy-7-[5-(2-n-propylphenoxy)pentoxy]-8-n-propylchromone → 2-Carboethoxy-7-[5-(2-n-propylphenoxy)pentoxy]-8-n-propylchroman-4-one

HRID 1285259Notes

Reaction equation

HRID 1285259 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][CH:27]=[CH:26][C:25]=1[CH2:30][CH2:31][CH3:32])[C:9]=2[CH2:33][CH2:34][CH3:35])([O:3][CH2:4][CH3:5])=[O:2]>O1CCCC1CCO.[Ni]>[C:1]([CH:6]1[CH2:15][C:14](=[O:16])[C:13]2[C:8](=[C:9]([CH2:33][CH2:34][CH3:35])[C:10]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[CH2:30][CH2:31][CH3:32])=[CH:11][CH:12]=2)[O:7]1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

4

Reactant 1

HCID 135378642-Carboethoxy-7-[5-(2-n-propylphenoxy)pentoxy]-8-n-propylchromone

Product 1

HCID 202504732-Carboethoxy-7-[5-(2-n-propylphenoxy)pentoxy]-8-n-propylchroman-4-oneYield 89%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 119895722-(Oxolan-2-yl)ethan-1-olSolvent

Procedure

961 mg (2 mmole) of the compound of Example 30 was dissolved in 30 ml of 50% tetrahydrofuran-ethanol and 96 mg of Raney Nickel was added. The resulting suspension was hydrogenated at 2 psi and room temperature for 30 minutes. After separation of the catalyst by filtration, the solvent was removed by rotary evaporation to yield 855 mg (89%) of the title compound as a clear oil. Calc: C, 72.17; H, 7.94; Found; C, 71.84; H. 8.00.

Workup

  1. customAfter separation of the catalyst
  2. filtrationby filtration
  3. customthe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-e8ae27c406884b58ba68010b349cbffc
Source dataset
uspto-grants-1986_01
Patent number
US04565882

Reaction notes

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