Cyclohexene → HCID 15650854, compound

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

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.).