Acryloyl chloride → HCID 86748209, compound

HRID 1708607Notes

Reaction equation

HRID 1708607 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11](=[C:14]([CH3:16])[CH3:15])/[C:10](=[C:17](\[C:21]3[CH:25]=[C:24]([CH3:26])[O:23][C:22]=3[CH3:27])/[CH:18]([CH3:20])[CH3:19])/[C:9]2=[O:28])=[CH:4][CH:3]=1.[C:29](Cl)(=[O:32])[CH:30]=[CH2:31]>ClCCl.C(N(CC)CC)C>[C:29]([O:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11](=[C:14]([CH3:16])[CH3:15])/[C:10](=[C:17](\[C:21]3[CH:25]=[C:24]([CH3:26])[O:23][C:22]=3[CH3:27])/[CH:18]([CH3:20])[CH3:19])/[C:9]2=[O:28])=[CH:4][CH:3]=1)(=[O:32])[CH:30]=[CH2:31]

Participants

5

Reactant 2

HCID 13140Acryloyl chlorideHCID 86748210HCID 86748210, compound

Product 1

HCID 86748209HCID 86748209, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution obtained by dissolving 1.13 g of n-(4-hydroxyphenyl)-2-[(E)-1-(2,5-dimethyl-3-furyl)isobutylidene]-3-isopropylidenesuccinimide obtained in Example 18 in 30 ml of dichloromethane, 0.62 ml of triethylamine, followed by dropwise addition of 0.36 ml of acryloyl chloride in 10 minutes. The reaction was carried out at room temperature for additional 30 minutes with stirring. After the reaction, the reaction solution was well washed with water, dried over anhydrous magnesium sulfate, and subjected to removal of the solvent by distillation. The resulting residue was purified by column chromatography (filler: Wakogel C-300, eluent: a mixed solvent of n-hexane and ethyl acetate) to give yellow crystals of N-(4-acryloyloxyphenyl)-2-[(E)-1-(2,5-dimethyl-3-furyl) isobutylidene]-3-isopropylidenesuccinimide in yield of 60%.

Workup

  1. customTo a solution obtained
  2. customAfter the reaction
  3. washthe reaction solution was well washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customsubjected to removal of the solvent by distillation
  6. customThe resulting residue was purified by column chromatography (filler

Sources & evidence

ORD record
ord-66a4808b37e542458a9bd64f94ef0325
Source dataset
uspto-grants-1994_10
Patent number
US05359085

Reaction notes

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