Cyclohexene → HCID 15650854, compound

HRID 1941229Notes

Reaction equation

HRID 1941229 reaction equation
[CH3:1][C:2]1[C:11]2[O:10][C:9]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:8][C:7](=[O:18])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:19]CC1C=CC=CC=1.C1CCCCC=1>C(OCC)(=O)C.[Pd]>[OH:19][C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[O:18])[CH:8]=[C:9]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[O:10][C:11]=2[C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 115954978-methyl-2-morpholin-4-yl-7-phenylmethoxychromen-4-one

Product 1

HCID 15650854HCID 15650854, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Part A: 8-Methyl-2-(4-morpholinyl)-7-(phenylmethoxy)-4H-1-benzopyran-4-one (8.59 g, 24.4 mmol.) is suspended in 250 ml of ethyl acetate. 9.9 ml of cyclohexene is added followed by 0.85 g of 10% Palladium on carbon. The mixture is heated at reflux for 18 hours. The reaction is allowed to cool and filtered, the solid is taken up in methanol, decanted and filtered. The methanol is evaporated to give 4.71 g (74%) of the phenol (mp>250° C.).

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 18 hours
  3. temperatureto cool
  4. filtrationfiltered
  5. customdecanted
  6. filtrationfiltered
  7. customThe methanol is evaporated

Sources & evidence

ORD record
ord-53e48daafc884dacb283e1db2953d2de
Source dataset
uspto-grants-1997_12
Patent number
US05703075

Reaction notes

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