3,5-Heptanedione → HCID 514307, compound

Reaction equation

[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH2:11][CH:12]=[CH:13][CH2:14][CH2:15]I)=[CH:4][C:3]=2[O:2]1.[Li].[CH3:18][CH2:19][C:20](=[O:26])[CH2:21][C:22](=[O:25])[CH2:23][CH3:24]>CN(C)C=O>[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH2:11][CH:12]=[CH:13][CH2:14][CH2:15][CH:21]([C:20](=[O:26])[CH2:19][CH3:18])[C:22](=[O:25])[CH2:23][CH3:24])=[CH:4][C:3]=2[O:2]1

Participants

Procedure

[I; Ar is 3,4-methylenedioxyphenyl, R0 is H, R' and R" are CH3CH2CO, Y is CH=CHCH2CH2 ] was prepared from 12.5 g. of 6-(3,4-methylenedioxyphenyl)-3-hexenyl iodide (Preparation D2) and 12.5 g. of the lithium salt of 3,5-heptanedione in 175 ml. of dimethylformamide. The product was chromatographed on silica gel and eluted with pentane-benzene (1:1) and then with chloroform-benzene (7:3). The latter brought out 7.0 g. of 4-[6-(3,4-methylenedioxyphenyl)-3-hexenyl]-3,5-heptanedione as a light amber oil.