3,5-Heptanedione → HCID 514311, compound

HRID 839159Notes

Reaction equation

HRID 839159 reaction equation
[CH2:1]([C:3](=[CH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=1)[CH2:4][CH2:5]I)[CH3:2].[Li].[CH3:21][CH2:22][C:23](=[O:29])[CH2:24][C:25](=[O:28])[CH2:26][CH3:27]>CN(C)C=O>[CH2:1]([C:3](=[CH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=1)[CH2:4][CH2:5][CH:24]([C:23](=[O:29])[CH2:22][CH3:21])[C:25](=[O:28])[CH2:26][CH3:27])[CH3:2]

Participants

5

Reactant 3

HCID 819233,5-HeptanedioneHCID 3028194LithiumHCID 54542682HCID 54542682, compound

Product 1

HCID 514311HCID 514311, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[I; Ar is 4-CH3O2CC6H4, R0 is H, R' and R" are CH3CH2CO, Y is C(C2H5)=CHCH2CH2 ] was prepared from 14 g. of 3-ethyl-6-(4-carbomethoxyphenyl)-3-hexenyl iodide (Preparation D10) and 14 g. of the lithium salt of 3,5-heptanedione in 200 ml. of dimethylformamide according to the procedure described above in Example 2. The product was chromatographed on silica gel and eluted with the pentane-benzene-ether solvent series. Benzene containing 2% ether brought out the desired product, 2.6 g. of 4-[3-ethyl-6-(4-carbomethoxyphenyl)-3-hexenyl]-3,5-heptanedione as a yellow oil.

Workup

  1. customwas prepared from 14 g
  2. customThe product was chromatographed on silica gel
  3. washeluted with the pentane-benzene-ether solvent series

Sources & evidence

ORD record
ord-5d1f1a476cac4f9495eda368351caf3f
Source dataset
uspto-grants-1978_06
Patent number
US04093736

Reaction notes

Loading…