2,4-Hexanedione → 3-[3-Ethyl-6-(3,4-methylenedioxyphenyl)-3-hexenyl]-2,4-hexanedione

HRID 839157

Reaction equation

HRID 839157 reaction equation
[CH2:1]([C:3](=[CH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]2[O:16][CH2:17][O:18][C:12]=2[CH:11]=1)[CH2:4][CH2:5]I)[CH3:2].[Li].[CH3:20][C:21](=[O:27])[CH2:22][C:23](=[O:26])[CH2:24][CH3:25]>CN(C)C=O>[CH2:1]([C:3](=[CH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]2[O:16][CH2:17][O:18][C:12]=2[CH:11]=1)[CH2:4][CH2:5][CH:22]([C:23](=[O:26])[CH2:24][CH3:25])[C:21](=[O:27])[CH3:20])[CH3:2]

Participants

5

Reactant 3

HCID 763552,4-HexanedioneHCID 3028194LithiumHCID 543734513-Ethyl-6-(3,4-methylenedioxyphenyl)-3-hexenyl iodide

Product 1

HCID 5143033-[3-Ethyl-6-(3,4-methylenedioxyphenyl)-3-hexenyl]-2,4-hexanedione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[I; Ar is 3,4-methylenedioxyphenyl, R0 is H, R' is CH3CO, R" is CH3CH2CO, Y is C(C2H5)=CHCH2CH2 ] was prepared from 23.2 g. of 3-ethyl-6-(3,4-methylenedioxyphenyl)-3-hexenyl iodide (Preparation D1) and 22.3 g. of the lithium salt of 2,4-hexanedione (prepared by the procedure described in Example 8 below) in 300 ml. of dimethylformamide according to the procedure described above in Example 2. There was thus obtained 21 g. of crude product which was chromatographed on 600 g. of silica gel in pentane solution containing 20% benzene. The column was eluted with the pentane-benzene-ether solvent series. Benzene containing 3% ether brought out the desired product, 14.5 g. of 3-[3-ethyl-6-(3,4-methylenedioxyphenyl)-3-hexenyl]-2,4-hexanedione as a yellow oil.

Workup

  1. customwas prepared from 23.2 g
  2. customof crude product which was chromatographed on 600 g
  3. additionof silica gel in pentane solution containing 20% benzene
  4. washThe column was eluted with the pentane-benzene-ether solvent series

Sources & evidence

ORD record
ord-2891f5efe7234ffea56fbb1638de4f3c
Source dataset
uspto-grants-1978_06
Patent number
US04093736

Linked notes

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