Toluene → HCID 57456871, compound

HRID 658249

Reaction equation

HRID 658249 reaction equation
[CH3:1][O:2][CH2:3]/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]([CH:13]=[C:14](/[CH:16]=[CH:17]/[CH2:18][O:19][CH3:20])[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10].C1(C)C=CC=CC=1.C1(S(NN)(=O)=O)C=CC=CC=1>CCOCC>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([CH2:16][CH2:17][CH2:18][O:19][CH3:20])[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 3

HCID 1140TolueneHCID 65723Benzenesulfonyl hydrazideHCID 57456870Methyl 3,5-bis[(1E)-3-methoxyprop-1-en-1-yl]benzoate

Product 1

HCID 57456871HCID 57456871, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of methyl 3,5-bis[(1E)-3-methoxyprop-1-en-1-yl]benzoate (1 eq.) from the previous step in refluxing toluene was added benzenesulfonohydrazide (5 eq) in five portions over 2 h. The reaction was stirring as reflux for 18 h. After cooling to rt, the reaction was diluted with ether. The organic extract was washed with 1 N aqueous HCl, brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by flash column chromatography (SiO2, 20% EtOAc in Hex) to afford the title compound as an oil.

Workup

  1. temperatureas reflux for 18 h
  2. extractionThe organic extract
  3. washwas washed with 1 N aqueous HCl, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography (SiO2, 20% EtOAc in Hex)

Sources & evidence

ORD record
ord-b1bcb487c77a41f4a782d110b154de33
Source dataset
uspto-grants-2011_12
Patent number
US08076359B2

Linked notes

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