Ethyl chloroacetate → ethyl [4-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-phenoxy]-acetate

HRID 2222356Notes

Reaction equation

HRID 2222356 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[C:11](=[CH:14]/[C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)/[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:12](/[C:11](/[C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[CH:14]\[C:15]1[CH:16]=[CH:17][C:18]([O:21][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:19][CH:20]=1)#[N:13]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 11430Potassium CarbonateHCID 10446442(Z)-2-(3,4-dimethoxyphenyl)-3-(4-hydroxyphenyl)acrylonitrile

Product 1

HCID 10384323ethyl [4-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-phenoxy]-acetateYield 34%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Compound 1 (281 mg) and ethyl chloroacetate (245 mg) were dissolved in acetone, and potassium carbonate was added to the resultant solution, followed by reflux for three hours. The resultant mixture was subjected to filtration, and insoluble matter was removed from the mixture. The resultant filtrate was concentrated to dryness under reduced pressure, followed by recrystallization, to thereby produce the target product (124 mg, yield: 34%).

Workup

  1. temperatureby reflux for three hours
  2. filtrationThe resultant mixture was subjected to filtration, and insoluble matter
  3. customwas removed from the mixture
  4. concentrationThe resultant filtrate was concentrated to dryness under reduced pressure
  5. customfollowed by recrystallization

Sources & evidence

ORD record
ord-2102ffc89b3b428fb6e9eec6dc6fcac6
Source dataset
uspto-grants-2008_05
Patent number
US07371773B2

Reaction notes

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